I am currently under contract on my first house hack / BRRRR in the south west side of the city.

As far as rentals go, I really like north west and southwest Des Moines proper for my investors.

I live just southwest of Chicago.

We live southwest of Houston, so I'm used to it

(I've been to two DCU games in the past year, but I dined at the Wharf at least thrice just in the last week.)I wouldn't use Southwest as an analogue to Chester.

Recently, my significant other and I have been spending time in rural southwest Wisconsin.

Located in Southwest Missouri.15 pads3 Currently Rented @ $150/month8 Park-owned homes in various stages of repair, 2 of which can be rented right now for ~$300/monthPurchase price = $32kDown payment = $3kI can do the work on them myself, and many of the materials are already included.

Needless to say I'm delighted it didn't go nearly that far.Columbus is a 3 hr flight from Denver, and fortunately Southwest runs two nonstops a day.

I am in the process of buying my first rental SFR in Independence, but not as a turn-key.The most important suggestion I have for you is to drive up to Ronkonkoma and buy a ticket to Kansas City from the friendly people at the Southwest Airlines counter. 

These days, we use the Southwest Visa -- we get points (which can be used towards free travel) and with $110,000 in spend per year, we get a companion pass so my wife (or whomever) can fly free with me.