I’d be hesitant to put yourself in a position where you’re cash poor since that's always when problems seem to arise. 

Patten Law Firm or American Title are two popular ones.

I guess I would say if the property is in a very popular/desirable part of town with a lot services/entertainment then even if there is homeless services nearby that increase that activity in the area you will do OK,  but you will constantly be dealing with some of the side effect (more trash, low level property crime, occasional trespassers, etc).   

Move in fees are popular in Chicago. 

I have read that Breckenridge is very popular but the median home price is nearly 700k.

The key is making sure fees and what you're getting for them are reasonable, and to be mindful of any assessments that will arise in the future.

Also you may want to add a few thousand to your 2nd position and build up your reserves.. your paying a very low rate for second position money and it could really help if the need arises.. you have enough juice in these to do that I think.. 

Hello all,As I have looked into short term property rentals it seems like a common problem arises when looking for a promising property manager.

Not sure if you've ever been up there in the spring but the blossoms on the trees are in full bloom and it's really pretty and becomes a really popular spot for photo ops.

Some people have great success with renting to people they know and others can find it challenging - just be prepared for all the different situations that could arise from renting to a friend.