Long Distance Real Estate Investing - David Greene (even if you aren't doing long distance, this is still great for systems that will make your life easier!)

In addition, for the raise even if it is close friends and family I would recommend using a software system like Syndication Pro, AppFolio, etc.

Pretty much every person who says they have a system or secrets to sell you to make you a success is a fake.

Not sure how many square feet the units are or how access is to duct everything (of course you can also use a ductless mini split) but your cost should be half that.Window units look terrible and eliminate the use of that window (for the most part).

Look into a ductless mini-split system.

If you need new central ac/heat system that will add $4-5K more.  

That makes it difficult to set up and maintain a system.

And the local utility company won't do things like energize  new panel box or turn on a new HVAC system without seeing the approved permit. 

Had success with our other STRs and have some strong systems in place.

Roofing - understanding how roof systems for your area work/are put together, also gutter systems12.