The Annual Owner Statement should break down all the expenses that the owner's tax professional then figures out how to deduct and on what tax schedule.So that way the owner can expense everything throughout the year?   

A sub-to calculator showing how much cash a seller can avoid bringing to closing.

. - What exactly is the red tape you are trying to avoid? 

@Drake BackmanBigger Pockets is a great place to find a tax strategist specializing in real estate taxation.A good real estate tax strategist can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding a tax  strategist specializing in real estate taxation, business taxation, financial planning and tax planning.Consider working with your tax strategist remotely to expand your options.I would also recommend looking for a tax strategist willing to work with you throughout the year.

Make sure to plan for the added rental income/ordinary expenses on your tax return. 

I want to avoid mistakes as a new landlord so hoping to learn from all of you! 

If I can park the 388k ($415-27k) for one year at CD rate of 4.5% and then est 300k (after paying cap gain/depr recap) at 3.0% (assume CD rates lower) that interest income of about 24 months net of ordinary income tax is about the same as my current mortgage.Trying to play devil's advocate and think why selling this year does not make sense. 

I would also share pros and cons of paying taxes on the windfall versus owner carry.

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

Definitely a question for a tax attorney/accountant, especially with the dollar amounts involved.