These contractors can be on the pricey side you'd want to make sure the #s work before considering a reputable contractor.

My vision is to keep it a while (it’s paid off) and use the cashflow to help with my kids college.  

Go ahead and file.In real life it costs you time to figure it out and money.

from a laptop or mobile phone on one of my SFR's (internet must be hooked up, but most tenants do it anyway and like to be able to monitor the outside of the house remotely, even if there's nothing going on.)

It also helps to identify how much capital, or access to capital, you have. 

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

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.

And since you hold the property with your wife in a trust that makes this a related party scenario. 

He still makes a profit off of the government share.