I have almost 100 properties there and this summer wiped out a lot of weaker players.

For the sake of this discussion assume I have a GC that is 100% capable of performing as the GC but is not licensed.  

They may be good at this game, and they know you are a new player.

A short sale will undoubtedly have an impact on that sellers financial capabilities even long after the property has been short sold to you.

There are many different ones, some set up for bigger operations and some set up for smaller ones.I used Building very briefly before I realized it was too small for what we were trying to do but from what I saw it made sense for a smaller operation (although to be honest I can't remember how good its bookkeeping capabilities are.We had a poor experiences with Property Ware but I don't know if they have improved it in the last 3 years.We currently use rent manager and I'm sure it would fulfill your needs, but It might be cost prohibitive if you don't have many rentals.There are hundreds out there but having a property management software that can double as your bookkeeping software can be a very nice set up.

In fact, if you take a look at the websites of some of the other players in the industry you'll find that we actually provide more information up front than most.

Nothing has changed except "playing field" and the "players". 

If you are not capable of keeping occupancy above 85% during a value-add renovation, assuming the property was purchased stabilized ~95%, then I highly recommend hiring a property management company experienced with a value-add lease up and GC to manage the process.

I also am former college basketball player (2 year captain at PLU), a volunteer coach in the community and am a part business owner in the catering business that operates the diner at the resort I live in. 

If you have a lobby area, most cams now are audio capable, and can be two way.