As for cashing out the investors, either refi after 2 years to see what else can be pulled out to pay them back, or worst case scenario, after year 4, sell 2-3 properties to pay them back.Does this seem like a reasonable exit strategy - namely seeing if I can pay back investors via refi, or selling off part of package if necessary in 4-5 years?

Provide a deal package that includes:PicturesEstimates of Renovation CostMaterials List on Home Depot Quote on PaperComparable SalesFiverr.com can help with After Renderings like on Fixer UpperPerform every act of due diligence you would do for a flip if your $100K was going into the deal. 

And they cannot separate the gym from the rest of the RE - it's a package deal.So I have some questions!

I'm out of my element as your question is for commercial, not residential, but IMO if owner planned to repaint anyway, just repaint and call it a day.

I bought a exam prep package with PrepAgent as I plan to really get down and dirty with studying.

You have to search for them, package them together and then work with great commercial mortgage agents.  

I like all of the features of the growth package that Buildium has, but it's kind of pricey.

Once you can demonstrate YOU are worthy of attention, then you can look at the deal together and build a package for it that will be presentable to the loan approval committee. 

Ideally, you would want the Property manager to have their own Liability coverage (both professional and general liability), Workers Compensation, and Crime coverage (either in a bond or as part of their BOP/Package policy) and name you as an additional insured under their policy.

But it never assumes jurisdiction over any element of the probate estate.