Most tax preparers don't know the difference between a rental investor and a dealer — and that difference can cost you thousands. We work with residential investors at all levels and understand the decisions, documents, and rules that come with owning and selling investment property.
Schedule a no-obligation call. We'll review your properties, find missed deductions, and make sure your rental and flip activity is structured for the best tax outcome.
No pressure. No obligation. Just clarity.Rental & flip-specific organizer
E-signatures + secure upload portal
Proactive quarterly guidance
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Schedule E income & expense reporting
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Depreciation & cost segregation
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Repairs vs. improvements classification
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Passive activity loss rules
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1031 exchange awareness
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Cost basis & improvement tracking
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Short-term vs. long-term capital gains
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Dealer status risk assessment
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Self-employment tax awareness
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Documentation for audit protection
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Quarterly estimated tax planning
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Entity structure guidance (LLC, S-Corp)
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Depreciation recapture planning
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Retirement contributions for investors
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Year-end check-ins (optional)
If you do both, getting the details right, and keeping the two activities clearly separated, matters a lot. Here's what we watch for on each side:
Maximizing depreciation every year
Classifying repairs correctly (deductible vs. capital)
Passive loss rules & income offsets
Keeping records clean for a potential 1031
Tracking basis for an eventual sale
Tracking every dollar of cost basis
Holding period strategy (short vs. long-term rates)
Monitoring dealer status exposure if you flip frequently
Self-employment tax if the IRS views activity as a business
Quarterly estimates to avoid underpayment penalties
"I have been using Tax Associates for years and Jonathan has always been very thorough and meticulous while doing my taxes. He's quick at responding to my questions and concerns; especially when filing for more than one state."
— Tiffany, Client
"Jonathan was a consummate professional, always answering any questions and going into depth on areas of concerns. I cannot recommend his services enough!"
— Fritz, Client
"He goes above and beyond answers, questions and emails almost immediately... Jonathan is amazing and I feel fortunate to have a honest, reliable tax consultant."
— Patricia, Client
Have questions or ready to get started? Send us a message and we'll get back to you shortly.