And I can't really talk shop with my inner group of friends (other than the macroeconomics of CRE).Are there outlets for these types of conversations? 

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.

I'm letting my PMLs mature after a 2 year experiment and going back into old-fashioned rentals.

There are multiple ways to do this, I personally have sent out direct mail in a few different fashions, and cold called as well.

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.

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