The other camp of investors puts off maintenance for as long as possible and essentially bleeds a property dry and may have trouble selling at the end because so many repairs have been deferred.

The fact is that your tenants probably don't contact your PM very much at all, so you are just bleeding for very little reason.Fourth: the tax consequences of selling your property, unless you 1031 seems to always get glazed over in these discussions. 

@Caleb Heimsoth  as Bob noted, there are people who will paint for $175/day but availability might be a big issue and it also depends on what quality you're looking for (e g does it matter to you that the old paint bleeds thru in a couple of spots)if you figure around $1.05-$1.10/sq ft (of wall space, not just floor space) that will put you on the low end of retail, will give you a decent quality job but won't include wall repair or baseboards/trimdry locking the basement should be around the same price but that stuff has a pretty overwhelming odor so you might get contractors saying they either don't do it or want a premium....get yourself a quart and open it up if you don't know what I mean....I've got a painter and other contractor referrals.....most will work anywhere on the west side. 

However, this has historically never worked out well.My husband and I used to be bleeding hearts for some of these types of "helpers", but after we discovered 1 living in one of our projects (explained why he was taking so long to finish), and 1 who hired his wife and her friend to be his grunts (not the best idea for manual labor), and 1 who brought his dogs (yes plural) to our flip project where everything was sparkly new...and then wasn't because dog slabber was the new finish....we decided that we needed to save our bleeding hearts for passion projects that didn't involve our RE business.  

Tough decision but as a rental this property will bleed money.

I would only worry about the possibility of bleeding when it rains, but that and the city taking them down is just factored into cost lost.Facebook is quirky.

Originally posted by @Philip Williams:@Erik S. Well

You typically have to pay a 3% balance transfer fee, so transferring $28,000 for example, you pay $800 or so, but then the bleeding stops and you have between 12 and 18 months (depending on the offers) to pay with zero interest charges. 

Cap rates have become so depressed that you will bleed out every month.

Yup, that pig that was bleeding him emotionally with the 16 tenants that he have to manage (or a property manager who is taking their cut of his table scraps) is now bleeding him financially as well.What would you do if I told you that "this widget I'm selling is currently giving me $100 per month BUT, it has the POTENTIAL to give me $300 per month if I invest MORE money AND TIME into it.