I would recommend looking at vacation properties that are more reasonably priced as opposed to something in Breckenridge.

Or hard money loans, which many times is explained as "cash" because it funds quickly (as opposed to a mortgage with a bank). 

I think you need to avoid placing the signs in the "right of way," as opposed to private property (possibly minimally maintained) that happens to be near a street.

can't be just lighting for the hallways/exteriors for two buildings.

I may end up doing a little painting on the exterior, but any expense would be minimal.

Same procedure for boiler/heating system but perform a separate test on this.Usually the elbows in runs near the exterior walls break first which actually reliefs other parts of system.I have seen freeze ups where it was only minor a few elbows here and there.It really needs to be done on a case by case basis but it seems like your preparedfor the worst but I don't think it will be that bad. 

I had the same issue in my SFR and was advised to grade the space so that the water would drain out along the foundation to the exterior. 

@Russell BrazilBased on recent experience with investor buyers I see the market for rentals tightening in some of the nice bread-and-butter neighborhoods (as opposed to the red-hot ones near the water).

Interior or exterior.  

I would hesitate to lock up HELOC funds in a buy and hold also unless you are absolutely opposed to doing some sort of cash out deal, either flip a property or BRRRR.