I always buy something I could see myself living in. not necessarily the colours, but the location and size of the home and the condition.

Getting a bit overwhelmed with all the required County Level and City Level business licenses, STR permits and Tax accounts (Business Tax, Franchise & Excise Tax, Sales & Use Tax) to register with the state.

We currently accept rent from tenants using a variety of 3rd party apps-Cashapp, Venmo, Zelle but are moving away from accepting payments in our individual names and want to start accepting payments directly to the LLC/business accounts, but LLC accounts do not accept Zelle and there is a fee for using business accounts on Venmo.

One property the square footage was high because they assumed both florrs were same size and they were not. 

Instead of their cash sitting in a savings account, they decided it would be a better investment to earn 3% on their money instead of .03% in the bank.

No one accountant is an expert in all areas in the tax code, so best to figure out what you want first in the world of real estate and then dive deeper there. 

You can run the same scenario accounting for the tax hit if you kept it past the 2 of 5 year time frame I presume you are referencing. 

My wife ordered a kid size pool table from China for our STR and they sent ear muffs.

Anyone answering is not responding as a Tax accountant, Insurance expert or as a Financial advisor.  

This is something I try to live by and teach my kids if I can - "A human being should be able to change a diaper, plan an invasion, butcher a hog, conn a ship, design a building, write a sonnet, balance accounts, build a wall, set a bone, comfort the dying, take orders, give orders, cooperate, act alone, solve equations, analyze a new problem, pitch manure, program a computer, cook a tasty meal, fight efficiently, die gallantly.