A lot of investors don’t realize this about short-term rentals:Your personal use can make or break your deductions.Here’s the big rule to know:If you use your STR personally for more than 14 days or more than 10% of the days it’s rented, the IRS may treat it as a mixed-use property.And once it’s mixed-use, your losses and deductions can become limited — or in some cases not deductible the way you expected.This is where STR tax plans quietly fall apart.Not because the investor did anything “wrong”… but because they didn’t track the days.The key is simple:- Track rental days- Track personal use days- Know where you stand before year-endIt’s not just about income and expenses — it’s about usage.STR owners — do you track your personal vs rental days consistently, or do you estimate it later at tax time?

I've learned most of what I know the expensive way.And the most expensive lesson of all was this: a "good deal" is whatever story you're willing to tell yourself at the time.The shift happened when I started underwriting downside instead of upside.The vast majority of brokers or agents pitch you the upside, and rarely inform you of the downside.

The thing that's been bugging me lately is I don't have a clean way to see how my whole portfolio is actually performing in one place.Like — I can run numbers on a new deal fine, but when I'm trying to figure out if I should sell one property to fund another, or refi vs hold, or just understand which of my properties is actually my best performer after all expenses...

I have a pretty good understanding of the rental market, my expenses, and how to find a deal.

Downside is money is typically more expensive. thats reason why many do not pull triggerdepends on person, I know some who are ok paying 12%+ 2 points on a $1M property as they figure ok they are spending an extra $30k on a deal but they can get it done a month or two faster which they may save that money in the long run. 

You're absolutely right that you can do it yourself.Key mistakes I see people make: 1. not getting the basis of property correct.2. missing expenses such as mortgage interest, property taxes, insurance, repairs vs capex, etc. 

Online custom screening and application, lease and other document signing, ACH payments, tracking expenses, automated late messages, viewing financials, uploading documents and pictures.

Context- 5 units are 1/1, 2/1, and 3 studios - It is Clearwater, FL in downtown - I am not particularly worried about maintenance/finding tenants given how impeccable the property is (had my contractors check it out) and tenant rent roll is strong (it rents well- list price: $650KThings that give me pause- tying up $186K in the real estate for a 3% cash return in the short term - I am bearish on long term appreciation for the downtown Clearwater market (it is a weird vibe)- I prefer buying in St Petersburg, FL but would I would have to accept subpar metrics (DSR/cash flow/etc) in exchange for good appreciation upside AssumptionPro FormaActualGross Rents $ 89,400.00 $ 84,600.00 Vacancy10.00% $ 8,940.00 $ 7,614.00 Prop Mgmt0.00% $ - $ - Cash Reserves3.00% $ 2,682.00 $ 2,538.00 Taxes (actual) $ 11,000.00 $ 11,000.00 Insurance (actual) $ 11,000.00 $ 11,000.00 Maintenance + Utilities8.00% $ 7,152.00 $ 9,550.44 Operating Expenses $ 40,774.00 $ 41,702.44 NOI $ 48,626.00 $ 42,897.56 Mortgage $ 37,593.68 $ 37,593.68 Cash Flow (NOI - Debt) $ 11,032.32 $ 5,303.88 Cash on Cash Return (Cash Flow / (Down Payment + Closing))5.9%2.8%Cap Rate (NOI / Purchase Price)7.5%6.6%Gross Rent Multiplier (Purchse Price / Gross Rents)7.277.68Operating Expense Ratio46%49%Debt Service Coverage Ratio (DSCR)1.291.14

If I know what everything cost and have a reasonable estimate of what useful life bucket each expense would go into is that not enough? 

The NY market is just so expensive that it feels hard to get started here.