So far I'm thinking buy and hold for a relatively passive income stream, but the more I've been reading, the more interesting opportunities I've been learning about!

That is not possible within IRS rules, other than by taking a (potentially taxable) distribution from the IRA.The questions I would suggest you ask are related to keeping the Roth IRA as a tax-sheltered vehicle.  

My goal is to learn the biz from the inside-out and slowly transition from active to passive income over the next decade or so. 

My end goal is to get another stream of income that will take me into a comfortable retirement.  

She even quit her full time job to pursue real estate full time, which has become a large challenge for us living on one income, and me being a senior airman.

I would recommend staying on the lower in when it comes to rental income expectations. 

Choose cities in safe and economically diversified areas with above-average income and population growth.

*However, I'll ask that the rental income will be mine after 9/20, instead of when we actually close.

Issues like....How is the income split.Who's name goes on the property.Who pays for taxes, insurance, maintenance.

How long must I rent my Chicago condo out before I can count the income toward another mortgage in Florida?