The biggest complaints about property managers is the lack of communication and personal service.

Welcome @Whitney Zelee..One of the first things i did when i started investing 2 years ago was getting the real estate license and that definitely helped me, especially with learning the market.Don't forget to join a local REIA.I personally like the Black Diamond networking event in Waltham. 

I've been pondering on withdrawing the money and using the funds towards updating my personal residence in preparation for renting it out.

I personally don't seperate my properties under different LLC's 

Personally in that market, I would say that a vacation rental should be in Class A shape for that market (Aspen).

PPS: I have been "studying" REI for some time now through BP and in person at the SJREI meetings.

Personally I wouldn't upgrade from 08 to current if I had to pay unless there's some new feature you really need.

I'm personally not a massive fan of 529 plans except in specific cases.

if it went through an actual foreclosure then as stated most if not all the junior liens should have been removed from title .. they still exist as to the person who lost the home.so something is no adding up.

I personally want to do some flipping but only to fund the buy and hold positions.