Bookkeeping, tax, and advisory services for small businesses across the greater Tampa Bay area.

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Real Estate Investors

We track every dollar by property so you know which units make money, which ones drain it, and where to invest next.

The Industry

An investor owns eight rental units spread across Brandon, Riverview, and Apollo Beach. Total rent collected last year was around $144,000. Total expenses including mortgages, insurance, repairs, and property taxes came to roughly $118,000. On paper, that looks like $26,000 in profit. But which properties made that money? Two of those units sat vacant for a combined five months. Insurance premiums jumped across the board in Florida this year. One property needed a full AC replacement in July. Another had a plumbing issue that required tearing into a wall. Without tracking by property, the investor has no idea that three of those eight units are actually losing money every month while the other five carry the load.

Real estate investing in the Tampa Bay area has its own rhythm. Rent comes in on the first of the month if you are lucky. Mortgage payments go out regardless. Property insurance in Florida keeps climbing and now represents a meaningful line item on every unit. Repairs are unpredictable and lumpy. Depreciation reduces your tax bill but never shows up in the bank account. The gap between what the bank statement shows and what your tax return requires is wide, and navigating it without proper records turns into guesswork.

Who This Covers

Buy-and-hold rental property owners, fix-and-flip investors, small commercial real estate investors, and syndication operators. Anyone in the Tampa Bay area building a real estate portfolio and needing accurate financial records to support decisions, taxes, and lender relationships.

What Makes It Complex

Every property is its own profit center. Mortgage payments need to be split between principal and interest for tax purposes. Capital improvements must be separated from routine repairs. Security deposits are liabilities, not income. Depreciation schedules run for decades and need to be maintained accurately. Add 1099s for contractors, rising Florida insurance costs, and passive activity loss rules and you have a level of complexity that outgrows a spreadsheet fast.

What We Handle

Every dollar of income and expense gets tagged to a specific property address. Rent collected, mortgage payments properly split between principal and interest, insurance premiums, property taxes, HOA fees, repairs, and management fees are all recorded at the unit level. QuickBooks gets set up with each property as its own class or location so you can pull reports showing exactly how each unit performs. When you want to know whether the duplex in Riverview is worth keeping or whether it is time to sell, the numbers are right there.

On the tax side, we maintain depreciation schedules for each property and track your adjusted basis as improvements are made over time. We handle the distinction between capital improvements that get depreciated and routine repairs that get expensed in the current year. Contractor payments get tracked so 1099 filing in January is already done. Schedule E gets prepared with clean, property-level detail. For investors with significant rental income, we set quarterly estimated tax payments so April does not bring a surprise bill. And if you are holding properties in LLCs, we handle the entity-level returns as well.

Property-Level Financial Tracking

Income and expenses tracked by address. Mortgage principal and interest separated correctly. Insurance, taxes, and HOA fees allocated to each unit. Vacancy periods recorded so you see actual occupancy rates and their impact. Monthly and annual reports that show net operating income per property, not just a blended total across the portfolio.

Tax Preparation and Planning

Schedule E prepared with property-level detail. Depreciation schedules maintained for each asset including improvements made after purchase. Capital improvements versus repairs classified correctly. 1099s prepared for contractors and property managers. Quarterly estimated taxes calculated based on actual rental income patterns. Entity-level returns for properties held in LLCs or partnerships.

Common Problems

Everything runs through one bank account and one general ledger with no property-level detail. The investor knows total rent and total expenses but cannot isolate performance by unit. A property that appeared to be a solid cash flow producer actually lost money after a two-month vacancy and a $6,800 roof repair. Meanwhile, two smaller units quietly generated strong returns all year. Without separation, the losing property stays in the portfolio and the investor does not realize where the real returns are coming from. Acquisition decisions get made on gut feeling instead of actual portfolio performance data.

Tax mistakes compound over time. A new roof gets expensed entirely in the year it was installed instead of being capitalized and depreciated. The cost basis of a flip property does not include the $14,000 in closing costs and holding costs that should have been added. Security deposits get recorded as rental income, inflating taxable income in the year collected. Depreciation gets missed entirely on a property because it was never set up. Passive activity loss rules are misunderstood, and legitimate deductions sit unused year after year. These are not small errors. They add up to thousands in overpaid taxes or create problems that surface years later during a sale or an audit.

No Property-Level Visibility

Total revenue minus total expenses gives you a number, but it hides the performance of individual properties. Profitable units subsidize underperformers and you cannot see it. You hold on to a property draining your portfolio because the blended numbers look acceptable. You buy more of the same type of property without knowing it is the weakest performer in your current holdings.

Tax Errors That Add Up

Capital improvements expensed instead of depreciated. Cost basis on flips that does not include all allowable costs, resulting in higher taxable gains than necessary. Depreciation schedules never started or maintained incorrectly. Security deposits treated as income. These errors cost real money at tax time and create headaches if you ever need to calculate gain on a sale or respond to an IRS notice.

What Changes

Each property becomes visible as its own investment. You see net operating income by unit and by property type. You can compare the return on your single-family rentals against your small multifamily holdings and see which category deserves your next dollar. Vacancy rates, maintenance costs, and insurance burden are tracked per property so you spot trends before they become problems. When it is time to decide whether to sell a property or refinance it, you have clean financials to support the decision.

Tax returns reflect reality. Depreciation schedules are current and accurate. Every capital improvement is properly tracked and added to basis. When you sell a property, the gain calculation is correct because the records have been maintained from the beginning. Deductions are captured throughout the year instead of scrambled together in March. Lenders receive organized financial packages when you apply for your next mortgage, and the process moves faster because the numbers are already clean.

Portfolio Decisions Based on Real Numbers

You stop guessing which properties perform and which ones drag. Cap rates calculated on actual operating data. Acquisition decisions informed by what your portfolio has already proven about different property types and locations. You buy, hold, and sell based on evidence rather than assumptions.

Tax Accuracy and Lender Confidence

Every deduction captured. Depreciation tracked properly from day one through disposition. Cost basis maintained so gain calculations on sales are accurate and defensible. When you walk into a lender’s office for financing on the next property, the financials are ready. Clean books open doors that messy records keep closed.

Tampa Bay's Small Business CPA Firm

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The Enterprise Management Group is a CPA firm based in Riverview, Florida, serving small businesses and nonprofits across the South Shore and greater Tampa Bay area. We provide bookkeeping, payroll, tax preparation, and CFO advisory services backed by decades of hands-on accounting and financial management experience.

Location

3905 Crescent Park Drive, 1st Floor, Riverview, FL 33578

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