I wouldn't feel comfortable keeping any prepaid rent if the unit is re-rented.

I personally will never buy a condo because of HOA.instead of staying in the same apartment, why not buy a duplex/multi-family and owner-occupy one unit?

@Menalik ArcherYou might want to listen to @Joe Fairless podcast #1054 with @Amy Wan from Bootstrap Legal for some thoughts on how to stay out of troublehttp://joefairless.com/podcast/jf1054-getting-paid...Cheers!

Your job at this point is to listen to your DB, stay calm, and communicate in a very businesslike manner.

You may want to leverage someone or ask the current owner to stay on for 12-18 months post closing in some form to assist with the transition.  

I am now a stay-at-home-mom with a 2.5 year old girl and a 1.5 year old boy.

I have a few condos in DC and they cashflow well, Just make sure to stay with the low-rise condo's and not the high-rise buildings, those are the ones that have insane HOA dues.

But as long as he keeps paying the 200 bucks I could care less, I would like to see it stay. 

For my first investment property, I thought I'd buy a multi family in the area I want to stay in long term even though it's a HCOL area.

I would go down there, but there are already enough people without a place to stay.