I've read through everything everyone has said, as well as carefully reading through the sales agreement and the final closing papers (that I did not sign but requested from the title agency)...

At settlement what is sold is the beneficial interest in the trust rather than the property itself.On paper the lender just sees a common estate planning tactic rather than a sale of the property.

@Sarah Taylor From a tax perspective, you would lose the STR tax benefit if you expect paper losses from the property.

Phone call with email follow up or email so there's a paper trail.

Always great to do research and not rush too quickly, but its almost always better when people "make the leap" sooner rather than later like you said, I'd recommend at least putting some pen to paper on a date/deadline to do your first deal versus someday

I see so many overpaying just because it looks good on paper. 

You need to do an independent review of the sold comps, DOM, and the finishes you need inside to get the ARV you see.3) When projects pass the paper test and pass the number tests, then you need a GC and an Agent or some kind of designer, who have already looked at all the comps, walk the space and put together a budget that works and that will get you the number.4) Now you need a good relationship with a money source. 

That leaves a paper trail and defeats the purpose of having a WY LLC. 

Write it down on paper and make it a goal that you'd like to find a house hack under a certain price point after being approved.

Tom,I completely understand the strategy you are looking to execute and accomplish when it comes to offsetting your W2 income with STR paper losses via cost segs and bonus depreciation.