Currently shopping around for a convention loan for first home to house hack.

That seems like a lot and I'd like to shop around -- can someone recommend an insurance agent or broker in Chicago?

A lot of borrowers shop lenders for days to find the "lowest rates" just to find out 3 weeks later that the lender cannot perform on their promise.

That's why my question was to go ahead all over the USA to see people's suggestions for better locations.The fact that you don't think it's silly to ask a forum to recommend any place in the United States for STR and expect to get answers from people without a funnel to sell you something is silly.Jersey City and surrounding is very good for MTR opportunities because of the proximity to NYC and since you are in residency, you would be MUCH safer focusing on MTR since you have an in to other medical professionals.

Seems much safer for everyone involved.  

My advice would be for sure to become a part of the FB group Short Term Rental Listing Advice through the Short Term Shop, Also become a part of the STS community and ask questions there and you will get a boost!

Get a strong shop vac with bristle brush and carefully clean off the condensing unit. 

So they'll help you pick the finishes and hand you a shopping list and then you do the rest DIY.

That just tells me real estate must just be a safer bet than dental offices from an investors perspective, which is great as I'm moving away from dental.

My father studied to become a plumber and my mother worked in a dry cleaning shop.