My goal is to be financially free and able to live anywhere, not confined to a market where my investments are. 

You can literally find answers to all of your questions within the confines of this site.

Till now I've kept things decently organized with a combination of Google Docs, coffee, and services like Lovely, Cozy, ApartmentList, etc (I have no affiliate with any of these services), but haven't quite found the perfect "Goldilocks" fit.  

When they say mother in law they really are not kidding its nice and cozy with the parking situation.

Hello,From the chatter on BP, I would say that Cozy and AppFolio are some of the more popular programs.I am not too sure of the price range, so that is something you may want to check out.Go on their websites and see if they have demos.

Only issues with cozy is 4-6 day gap of transferring the ACH; no way to record expenses and record backdate payments (its meant for an ACH method).

Also get near their open car door, smokers always smoke in their car and it’s usually strong smell due to the confined space.

While I want the home to be nice and cozy for myself, I also want it to be an excellent investment.

We currently use excel for our P&L and expense management and cozy or check for rent.

I've been renting by the room and have had great success using Cozy for rent and bills.