Tax planning & accounting. Beyond tax season.

Taxstra provides comprehensive tax preparation, strategic tax planning, bookkeeping, payroll services, IRS representation, and specialized consulting for real estate investors, physicians, and business owners.

We bring planning, preparation, and accounting into the same conversation. Our work focuses on physicians, business owners, real estate investors, and high-income households whose decisions need to be considered together. We explain the options and follow through on the work in your engagement.

Tax preparation uses your records to report the year’s activity. Tax planning looks ahead at decisions you can still make, such as buying a property or changing how you pay yourself. The plan and the return need to stay connected.

Yes. We work with clients in all 50 states from our office in Springfield, Illinois. Documents move through our secure TaxDome portal, and we meet by phone or video, so you can work with us wherever you are based.

We begin with a free 30-minute conversation about your situation and the help you need. If we agree to work together, your proposal sets out the scope and fee. Detailed return review and planning begin after engagement, followed by the implementation and filing work included in that scope.

Engagements are scoped after your free consultation. Fees depend on the complexity of your situation and the work involved, and your written proposal lists the fee and scope before any work begins. No surprises.

Bring us in while you are considering a decision. A new job, business, or property purchase gives us something concrete to work through together. You can also start with a review of your current arrangements if you want to understand what deserves attention this year.

If you expect to owe at least $1,000 in tax after subtracting your withholding and refundable credits, or if you are self-employed, you generally need to make estimated tax payments quarterly to avoid penalties.

Contributing to tax-advantaged retirement accounts like a 401(k), SEP IRA, Solo 401(k), or Traditional IRA can reduce your taxable income for the year while helping you build a nest egg for the future.

It depends on your income level, business goals, and liability concerns. An LLC offers flexibility and protection, while an S-Corp can provide significant tax savings on self-employment taxes for profitable businesses (generally above $50-70k net income).

Yes, as Enrolled Agents and CPAs, we are fully authorized to represent taxpayers before the IRS. We can handle all communications, attend meetings, and negotiate on your behalf so you never have to speak with the IRS directly.

Don't panic, but don't ignore it. Send a copy of the notice to us immediately. We will review it, explain what it means, and help you draft the appropriate response within the required timeframe.

The IRS generally recommends keeping tax returns and supporting documents for at least three years. However, for property, business assets, or if you underreported income by more than 25%, you should keep records for 6-7 years.

Accurate bookkeeping ensures you have a clear picture of your financial health, makes tax filing easier and more accurate, helps you manage cash flow, and is essential if you are ever audited.

If you use a portion of your home exclusively and regularly for your business (and you're self-employed), you may be able to deduct a percentage of your home expenses, such as mortgage interest, insurance, utilities, and repairs.

The IRS treats cryptocurrency as property. This means you may owe capital gains tax when you sell, trade, or spend crypto if it has increased in value since you acquired it. We help track and report all crypto transactions.

We'll need W-2s, 1099s, investment statements, property records, business income/expense summaries, prior year returns, and any relevant receipts. Our secure client portal makes uploading documents easy.

Yes, we offer flexible payment options for our tax planning and preparation services. We can discuss payment arrangements during your initial consultation to find what works best for you.

For 2026 the State and Local Tax (SALT) deduction is capped at $40,400 ($20,200 if married filing separately). The cap phases down by 30% of modified AGI above $505,000, but never below $10,000, and it is scheduled to return to $10,000 in 2030. Many high earners above the phase-down still land at the $10,000 floor, so PTE elections and business structuring still matter.

Absolutely. We specialize in helping clients get caught up on unfiled returns and negotiate with the IRS on back taxes. The sooner you address this, the more options are available to resolve the situation.

The 'STR Loophole' (Reg. Section 1.469-1T(e)(3)(ii)(A)) allows you to reclassify rental losses as non-passive if the average stay is 7 days or less and you materially participate. This means your rental losses (depreciation) can offset your active W-2 income, even if the property is in Florida and you live in Illinois.

A 1031 exchange allows you to swap one investment property for another of like-kind and defer capital gains taxes indefinitely. You must follow strict timelines: 45 days to identify replacement properties and 180 days to close.

Cost segregation is an engineering-based study that accelerates depreciation on your property by reclassifying components (carpet, fixtures, landscaping) into shorter depreciation periods (5, 7, or 15 years vs. 27.5 or 39 years). This provides massive upfront tax deductions.

Real estate offers numerous tax benefits: depreciation deductions, mortgage interest deductions, property tax deductions, 1031 exchange deferrals, opportunity zone benefits, and the potential for capital gains treatment on sales.

Yes! After a cost segregation study, the personal property components (5, 7, and 15-year property) can qualify for 60% bonus depreciation in 2024 (phasing down each year). This can create significant first-year deductions.

REPS allows you to treat all your rental activities as non-passive, enabling rental losses to offset any income. You must spend 750+ hours in real estate activities AND more time in real estate than any other profession.

LLCs provide liability protection and flexibility. For tax purposes, single-member LLCs are disregarded entities. For multiple properties, we often recommend a holding company structure with separate LLCs for each property.

Keep detailed records of all income and expenses, including repairs, improvements, insurance, property management fees, travel to properties, and supplies. Use separate bank accounts for each property and categorize everything in your bookkeeping system.

Repairs (fixing a leak, repainting) are deductible in the current year. Improvements (new roof, renovation) must be capitalized and depreciated over time. The distinction matters significantly for your tax planning.

Yes, travel expenses to manage, maintain, or collect rent from your rental properties are deductible. This includes airfare, hotels, rental cars, and meals (50%) if the primary purpose is business-related.

Moonlighting income is ideal for aggressive tax planning. We restructure this income through an S-Corp or LLC to deduct business expenses, fund a Solo 401(k) (up to $69k+ annually), and use PTE elections to bypass the $10k SALT cap.

We start with a free 30-minute initial consultation to verify fit. If we proceed, we perform a Deep Dive analysis of your prior 2 years of returns, build a forward-looking Tax Plan (entity structure, retirement, real estate), and handle your filings year-round.

If you have $50k+ in net 1099 income, an S-Corp can save you thousands in self-employment taxes. We analyze your specific situation to determine the optimal salary/distribution split and potential savings.

For employed physicians: max out 403(b)/401(k), backdoor Roth IRA, and HSA. For those with 1099 income: add a Solo 401(k) ($69k+ contribution) or defined benefit plan ($200k+ for older physicians).

Maximize pre-tax retirement contributions, review your W-4 withholding, utilize HSA accounts, consider real estate investments with accelerated depreciation, and if married, review filing status and income splitting strategies.

High-income physicians can't contribute directly to a Roth IRA. The backdoor strategy involves contributing to a non-deductible Traditional IRA, then immediately converting to a Roth. Be cautious of the pro-rata rule if you have other IRA balances.

Absolutely. Many physicians use short-term rentals with the STR Loophole to generate passive losses that offset their high W-2 income. Combine this with cost segregation for accelerated depreciation and significant tax savings.

A defined benefit (pension) plan allows for contributions of $200k+ annually, far exceeding 401(k) limits. It's ideal for older physicians with high, stable 1099 income who want to accelerate retirement savings and reduce taxes.

Locum tenens physicians often work in multiple states. We track your days worked in each state, file the required returns, and ensure you get credit for taxes paid to avoid double taxation.

If you are on an income-driven repayment plan, your monthly payment is calculated from your tax return: your AGI and filing status drive the number. Pre-tax retirement contributions lower your AGI (and therefore the payment), and MFS vs MFJ determines whose income counts. We model the tax side of those decisions; we do not advise on loan or repayment plan selection.

Generally, once your net business income exceeds $50-70k annually, the self-employment tax savings from an S-Corp exceed the additional costs (payroll, compliance). We'll model your specific situation to find the crossover point.

We offer full-service payroll processing through ADP, including paycheck calculation, direct deposit, tax withholding, quarterly 941 filings, annual W-2/W-3 preparation, and state unemployment reports.

Yes! Wages paid to your children under 18 in a sole proprietorship are exempt from Social Security and Medicare taxes. Their income up to the standard deduction is tax-free, and they can contribute to a Roth IRA.

Most ordinary and necessary business expenses are deductible: office supplies, software, professional services, insurance, advertising, travel, meals (50%), vehicle expenses, and more. Proper documentation is key.

The QBI deduction allows eligible business owners to deduct up to 20% of their qualified business income. Limitations apply based on income level, type of business (SSTB), and W-2 wages/property basis.

You must pay yourself a 'reasonable salary' subject to payroll taxes. Any remaining profits can be distributed without payroll taxes. We help determine the optimal split to maximize tax savings while staying IRS-compliant.

The Augusta Rule (Section 280A(g)) allows you to rent your home to your business for up to 14 days per year tax-free. The business gets a deduction, and you receive tax-free rental income. Documentation is critical.

You can use the standard mileage rate (67 cents/mile in 2024) or actual expenses (gas, insurance, depreciation). Keep a mileage log documenting business purpose, date, and miles. We'll determine which method saves you more.

Self-employed individuals can deduct 100% of health insurance premiums for themselves, spouse, and dependents. S-Corp shareholders must include premiums in W-2 wages, then deduct on their personal return.

Options include SEP IRA (up to 25% of net earnings), Solo 401(k) ($23k + 25% employer contribution), SIMPLE IRA, and defined benefit plans. The best choice depends on your income, employees, and savings goals.

Waiting until tax season to plan, missing estimated tax payments, not maximizing retirement contributions, ignoring entity structure optimization, and failing to document deductions properly. Proactive planning prevents these issues.

Maximize retirement contributions, harvest capital losses, bunch deductions, utilize HSAs, consider charitable giving strategies (donor-advised funds, QCDs), and structure your business and investments efficiently.

Tax-loss harvesting involves selling investments at a loss to offset capital gains. These losses can offset gains dollar-for-dollar, plus $3,000 of ordinary income annually. Unused losses carry forward indefinitely.

Take whichever is higher. The 2024 standard deduction is $14,600 (single) or $29,200 (married). If your mortgage interest, property taxes, charitable gifts, and state taxes exceed this, itemizing may benefit you.

Many states allow pass-through entities (S-Corps, partnerships) to pay state income tax at the entity level. This provides a workaround to the $10,000 SALT cap, potentially saving thousands for owners in high-tax states.

Short-term gains (assets held one year or less) are taxed as ordinary income. Long-term gains (held more than one year) are taxed at 0%, 15%, or 20% depending on income. High earners may also pay a 3.8% Net Investment Income Tax.

Income shifting involves moving income to family members in lower tax brackets through legitimate means like hiring children, gifting appreciated assets, or family limited partnerships. Done properly, it's completely legal.

This depends on your expected tax rates in each year. If you expect lower income or rates next year, deferring income makes sense. If rates will increase, accelerating income and deductions becomes the better strategy.

Donor-advised funds allow bunching multiple years of gifts, Qualified Charitable Distributions (QCDs) from IRAs reduce AGI, and donating appreciated stock avoids capital gains while providing a full deduction.

Investing capital gains in Qualified Opportunity Funds defers and potentially reduces those gains. Hold for 10+ years, and any appreciation on the OZ investment is tax-free. It's a powerful tool for real estate investors.

Common triggers include: high income with unusual deductions, discrepancies between reported income and 1099s/W-2s, excessive charitable contributions, cash-heavy businesses, home office deductions, and claiming hobby losses as business losses.

You have the right to professional representation, to know why you're being audited, to confidentiality, to appeal any decision, and to request an extension if needed. You never have to meet with the IRS alone.

The failure-to-file penalty is 5% per month up to 25% of unpaid tax. The failure-to-pay penalty is 0.5% per month up to 25%. Always file on time, even if you can't pay, the filing penalty is much higher.

Yes, through an Offer in Compromise (OIC), the IRS may settle for less than owed if you can prove paying in full would cause financial hardship. We can evaluate your eligibility and negotiate on your behalf.

File Form 4868 by April 15th for an automatic 6-month extension to file (not pay). If you owe taxes, estimate and pay by April 15th to avoid penalties and interest. We can handle this filing for you.

Generally, the IRS has 3 years from filing to audit your return. This extends to 6 years if you underreported income by more than 25%, and there's no limit for fraud or unfiled returns.

If your spouse or ex-spouse improperly reported items on a joint return without your knowledge, you may qualify for innocent spouse relief and not be held liable for the resulting taxes, penalties, and interest.

We can help you request an installment agreement. Short-term plans (120 days or less) have no setup fee. Long-term plans have fees but allow monthly payments. Staying compliant with all future filings is required.

Don't panic, you have options. We can help you set up a payment plan, request Currently Not Collectible status, or negotiate an Offer in Compromise. The worst thing to do is ignore the problem.

Yes, if your foreign accounts exceed $10,000 at any point during the year, you must file an FBAR. Additional reporting (Form 8938) may be required depending on your filing status and asset values. Penalties for non-compliance are severe.