You can't sit here and take a property that's bleeding north of $5k/mo in rent. 

Big jury award in a personal injury type lawsuit, or spouse and/or children wresting control away from you when you get older, or one bad deal for one property bleeds over the makes the others vulnerable, or you find yourself unable to pay huge tax liability at some point and want to be judgment proof on paper so IRS cannot seize assets and has to do an offer in compromise with you?

Property has been on the market to sell or lease every since (and clearly bleeding cash!)

Think of a shorties finger bleeding out

It’s run by a political machine that is bleeding it dry.

In addition, from an accounting perspective there is no return until negative position has been recovered regardless if you sell or refi.If Piti is $4800 and rent is $4k to $5k, you would bleed negative cash flow.  

@Ruchi Patel if the walls need repair from damage, like painter will itemize special primer or cleaner so crayons don’t bleed through, then my understanding is you can charge them for that part of the job, but only if it’s an additional charge above the normal paint job fee.

Part of your analysis paralysis may be because these two world are bleeding together in your situation. 

Obviously, we would do that 30 year loan option otherwise you would be bleeding money....I mean, you will still be significantly negative going this route even with the 30 year loan, but you can still have a low downpayment option if you want to purchase move-in ready homes. 

Raise your hand if you want to be on the bleeding edge of the law.blank_rome_whitepaper_on_attorney_opinion_letters.pdf (mba.org)