As far as one big plus to explain to him, is that if you buy it he won't have a shot sale on his report, which lenders look at the same as a FC.

I would have a contractor walk through it with you with the inspection report in hand to get a good repair estimate.

Look closely at a few grant apps and reporting metrics requirements and tell me what you think....

Yes, you will report the value of the money you converted to a Roth as taxable income for the year in which you do the Roth conversion.  

Take a trip over to the HOA management office and ask for a copy of the budget also, look up the HOA at the corporation commission's website, they may be required to publish budgets with their annual report.

Call the city to report the problem...

You report and pay taxes exactly the same way in a rental, regardless of whether it's held in your personal name or in an LLC.The issue of passive losses being locked up (they are not permanently lost) for high wage earners is difficult to get around unless you can qualify as a real estate professional (which is devilishly difficult to do).

LEADS, LEADS, LEADS.The daily court reporter in your county publishes a list of Divorce, Probate, Bankruptcy, Tax liens, evictions and foreclosure suits.  

Trained Reporting Officer for AML (may be the same as the Compliance Officer in a small company)5.

Walk-throughs with maintenance reports would likely not be cost effective for them to do.