Lender wise talk to @Zack Karp or @Jose Valdovinos...all of those folks work mainly with invetors and have a great pulse on the Chicago market.

IMHO, the main issue with what you described is that the disposition of the DST property, may not coincide with your next upleg acquisition.

Some investors find success doing mainly MTR and open up some dates for STR in between contracts.

When I search properties mainly in Punta Cana I always run into sites where condos are in development and have about 1 - 2 years till completion.

Quick tip: When you find a meetup that interests you, check the organizer's post history and engagement in the community - it's usually a good indicator of their true intentions.

@George Bell my LLC's do two main things:1) Hide my identity, so tenants can't easily find me. 2) Separate my business and personal assets, income & expenses, not so much for tax purposes, but to avoid IRS issues.-- Just audited by IRS this summer for first time ever and had no issues!

Did you buy the homes with the intention of going that route or did you own them already and pivot to capitalize on the opportunity for the increased revenue?

I have no plans to invest in here.In Midways I'm investing mainly in OH but I'm thinking of other cities/states around Lake Erie.How about you?

Go to networking events and be intentional about who you're looking to meet that day and what kind of value you'd like to add to them.

Mainly finding housing that I can profit from with an assignment fee.