And yet I don't have the time or the ability to manage STRs since I'm always gone.

Curious if you or @Zach Lemaster has any perspective to share on the ability to find a property from which you can retrieve a sizable-enough amount of equity to repeat the process.

The return needs to have ability to noticeably improve life.  

It was a little frustrating because I'd been in communication with these lenders from very early on, sharing all details with them from the start and repeatedly remarking on the Trust ownership, and stayed in contact with them throughout the discovery process as I firmed up everything on my end, and now I have the plans, the contractors, the OOP funds, and basically everything else ready to get started within 1-4 months, but I'm back at square one re: loan.

For example, you could find deals that have good long-term potential and buy enough money down so they throw off a bit of cashflow, but not so much equity that it limits your ability to scale.

The cost for this will be about $8000 vs the ability to get $500/month in rent which is a much better option.

Yes, tax advantages, appreciation - but most importantly: the ability to leverage! 

The latter eh that's when you see folks get ruined.Overall best to let the village handle it, like they did with the Indiana guy if that's who we are talking about.Folks are coming upon hard times, and I'm seeing more scams than ever and even when I'm out of the country the creativity is remarkable.

Im hesitant because I dont want it to interfere with my ability to secure financing in the future and frankly I not interested in taking on the risk without any potential reward.1. 

I'll be impacting the garage and yard, and would rather be in a position to not even deal with this as a negotiating point since the reality is whether I'm right or wrong, the tenant has the ability to make it more difficult if they're not happy.