He contacted an attorney, who finally got clarification from my attorney as well as the county recorder.  

Bonus depreciation will finally be phased out in the 2027 tax year This is well said

You state there's a lot of deferred maintenance, then state it is a remarkably well maintained property.

This works out well in instances where a very small home underutilizing a very large lot. 

As I see it, the only ways that real estate pays you well in the first 3-5 years is low to no leverage or a strategy that requires more work (short term rental, mid term rental, rent by the room, etc.).  

Many of the loans we see also are not well underwritten and properties are at 125%+LTV2.

*Cracks neck* Well, it's a journey for sure.

do you add bathrooms and convert the garage to rooms as well?

If you're not sure of you preferred direction with your next property I would invest in understanding investing more thoroughly and read 5-10 books as well as speak to other experienced investors.

Well if you ran realistic conservative numbers for maintenance, capex, vacancy rates, rental income, etc then you don't really need cash flow do you?