Unless you're locking up 10 acres in a large metro where a DR Horton or KB homes might come in, thats a little less localized.

Personally, I’ve been looking for ways to align creativity with the numbers, whether that’s finding undervalued properties, building relationships with local agents, or pivoting to new strategies.

I would vet contractors by finding local real estate agents that also work with investors, and/or a rehab investor in your area that does a lot of deals.

Ensure the sublease is explicitly permitted in a written agreement with your friend and aligns with local STR laws.

When I had my B&Bs we also included local restaurants and attractions in the packet of information which you might want for a STR.

Locals know that and you can see that in DOM. 

If you want to chat sometime I am local. 

Is there someone local who handles these sales? 

I completed an internship in commercial real estate, and I also attended a couple of local REIA meetings/networking events before moving to Northern VA.I was able to narrow down potential strategies, and I figured both BRRR as well as wholesaling don't seem to be the best strategies for me.

I would recommend finding some local meetups to attend, and also tuning into the Straight Up Chicago Investor's Podcast.