Start small - get yourself a househack, learn from your own experience of owning the rental property you live in, continue to educate yourself with reliable resources, and then worry about the next home.Having just one solid investment will put you ahead of most Americans than trying to find a way to buy 10 doors out of state in an area you don't even understand. 

Also with the population growing due to foreign plants opening shop there. competition can be very fierce & properties left for auction is minimal.

Out property value jumped in the last few years and big companies such as Amazon are setting up shop here.

Now I'm shopping around for an attorney to proceed. 

I would shop local to your STR.

The costs to purchase and hold real estate are continuing to increase requiring most Americans to devote nearly 50% of their income to housing expenses.

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!

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

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

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.