Insurance-  we had 18 months of full lost income coverage.  

I have all the income and expenses.

Transcribing transactions from bank statements, posting transactions to the correct accounts, and then manually creating an income statement, statement of owner's equity and a balance sheet is a fairly time consuming process and I have not been able to keep up with the book keeping between my regular work responsibilities.What accounting software do people recommend? 

Diversification into multifamily also lowers risk compared to a single rental, as vacancies won’t affect your income as drastically.3.

Since my adjusted basis is about 50K, am I going to have a $250K gain on my income taxes this year?

Getting a property with a partner / friend will not help you from getting hosed on taxes.I wouldn't move forward - You mentioned beng a high income earner so your hourly rate is very high.

But with that one lender I found I am not lendable due to not having proof of income for the last two years.

One thing to be aware of is the FHA multifamily self-sufficiency calculation which determines if a property can generate enough rental income to cover its mortgage payments.

Look into a DSCR, Debt Service Coverage Ratio, loan where the rental income can be used to qualify the cash out refinance instead of your personal income.To Your Success! 

May not be your cup of tea but they are cost efficient and they work to add passive income at a fraction of the cost to build a SFH.There are a few "Tiny Home" builders in Tampa and Manatee doing a ton of business.