Not everyone is a professional investor or contractor background.

The only thing that would be different is that Proper covers revenue loss + all the bells and whistles  I feel I don't need for 2x the cost - squatters/bed bugs.Any input on this from more experienced STR investors or others with insurance backgrounds please?

Also, since it would be a single member LLC in my wife's name, I'd end up getting a property management company since I, not being a member, would technically not have any liability protection in this scenario.Is there a way for the land trust to "gift" the property to the LLC, thereby providing carryover basis?

Many of them are savvy marketers but don't have background/experience in pref equity space but lead folks to believe it's just an  'easy button' to make stellar returns. 

Sometimes you just need to do what YOU want to do even if it isn't "technically" the best option from a financial standpoint. 

I used it primarily because I love the formatting and depth of info the background checks.

Technically, this may not meet your qualification standards, because you can’t ask your standard reference check questions.

Still figuring out how the technical stuff on the forum works but thanks to everyone that replied to my welcome to BP!

Just be wary that technically, according to Chicago's Airbnb ordinance, you can only operate 25% of the units in your building as Airbnbs.

A few other resources that offer funding opportunties for blighted and/or brownfield site renovations are MPCA, Kansas State Technical Assistance to Brownfields, DEED, LISC.