‘Large out-of-town institutional investors also are more likely to neglect properties, resulting in poor conditions for tenants.’I feel the exact opposite is true and from my experience many home owners in the city do not keep up their properties and their lack of upkeep is quite a pain when they are neighbors to your tenants (pests/rodents/water intrusion/etc). 

Spend some money up front to save yourself a lot of pain.

From there, you can get a more true estimate and avoid the financial pain of just plugging in a number.And, kudos to you for asking these tough questions and planning for tough events. 

HOA was a huge pain in the butt.

Hi all, I have llc set up for my rental and everytime new tenant move in I need to go bank open a new business escrow account is a pain.

Starting with lowest balance debt first is for the psychologically weak aka Dave Ramsay style.  

What your talking about is a subject to and a lease option combination both of which can be done but with the lease option it can not look like a disguised sale or you will have to deal with Dodd/Frank which can be a pain or so I've heard.

The paper work is more painful than writing the check in my opinion.  

Try to get to the bottom of why they're selling, what's their pain/motivation, and how can you help them solve that problem.

So when a problem or failure comes my way, I'm fist bumping myself because I know that it's just the growing pains of progress.