After 45 + years as a real estate investor, broker, lender, fund manager and syndicator, I’ve become aware that the “dream” of many investors and investor “hopefuls” is to be able to generate enough cash flow to live off their real estate holdings and accumulate enough wealth to make “work” optional.

It might make the most sense to just sell your primary residence and use it as 40% to 50% down payment on your future home. 

Welcome to BiggerPockets, Lucas! 

I then bought the house in Anchorage when she wanted to move back to Hawaii.

You'd want to work with the REIT sponsor and your CPA to understand the expected timeline for this a bit more.  

Hi Steve, welcome to BP!

He still makes a profit off of the government share.

It's going to depend on the lender, how it's titled and what kind of refinance you are doing.If you're doing a conventional cash out refinance, a lot of lenders are going to require a 3 to 6 month seasoning period prior to refinancing and it will have to be rented first.

Now, you need to figure out how to find deals and pay for them.