Don’t put your money into a new market without getting a firm handle on the data first. 

I worked for high end CPA firms for years and unfortunately while we said we were experienced with real estate clients- it was very surface level. 

Needless to say, I’m a firm believer in contributing as much as you can as early as possible to see that money compound every several years.That being said, my roommate and I are “on the clock” with our investment plans.

I have not had this happen before, and wonder how I could possibly give them a firm amount given that I have not done any move-out inspection.  

It's important that you have a firm grasp on everything before committing capital so you can limit mistakes.

I also recently had an employment change as I Conceded my 50% ownership share of a general contracting firm.

I've been working for a real estate appraisal firm for the past 15+years, specializing in residential real estate. 

This will either allow that agent to have another broker in their firm represent you through the transaction- or it will make the listing agent represent both of you by "stepping back" and acting more as a referee than a coach.

So I just started working for my parent's property management firm and things seem to be done super mom and pop style aka inefficiently.

The firm I used in NY didn't charge me for asking some questions.