I'm ok sacrificing some returns for hiring out anything that takes longer than about 15 minutes, and at this point am pretty much assuming that I'll be using property managers.  

So, I need a contract, I assume I will do a title search, have the land surveyed, hire a lawyer (I have one through work that will do RE stuff) to deal with title transfer and filing or is that someone else?  

Hire a professional to give you a quote.

The staining could be becasue these heaters draw air in from the bottom and push it out the top. so any dirty air  is pulled through the heater and pushed out the top causing stains on walls. 

Also, if you're not skilled at rehab design (interior/exterior design), I HIGHLY recommend you hire a designer.  

Hello to all that took that time to read this post, I’m a 22 year old husband to a wonderful wife and father of a beautiful baby girl and Im joining the United States Air Force to work on airplanes, but I’ve wanted to do real estate since I was in my early teens.

If you have the funds, you could save time and hire a professional cleaning service to do a thorough and nice job for you.

So selling an annual rental and purchasing vacation rental or air bnb or factory would all be fine. 

Since then I have also hired a property management company in Maui to run 1 of the condos.  

You either need to proactively seek the information, or hire advisors and pay them for their expertise.