It is always nice to live close to your rental properties (although not absolutely necessary), and as a military guy you are able to choose where you retire to.

@Kaaren Hall after seeing your post i called them right away, their fees are extremely high for an HSA that for the most part most people don't have a lot of money in.I max my HSA every year, but if you have a self only plan you can only put about 4k /yr  and if you have some medical bills it's less.they are also very restrictive on taking money out, and no CC to pay the doctor. prior to speaking with them I was extremely excited to see this opportunity you suggested,  but after my conversation I'm no longer...I will look for other options now that I see there may be some, so thanks so much for bringing it up.

I currently live Levittown and a house around the block from me is on the market for 1.5m.

Would love to keep this conversation going.

I live in the Champaign area.

Live under your means and start thinking about investing in Real Estate.In your position the thought of finding a duplex to house hack, live in one side and rent the other. 

I live in Florida but my family is from Portsmouth and I just there for Labor Day.

Also, what if I can't find people to live in the home?   

Ever since that conversation I went on a deep dive of research and studying to figure out how to accomplish these wild ambitions of mine.She helped me get my first property when I was 24 years old, which we ended up selling after a few years and using the revenue to purchase another property.

You have the ability to sell while limiting your capital gains tax because you lived in 2 of the last 5 years.