It seems that 150k could go a long ways towards that goal.

The barrier to entry is lower so they seem attractive, and to the person who knows what they are doing, they can be very profitable.

Cheap toilet paper makes a place seem cheap.   

First and foremost, I'm in Minneapolis / Saint Paul, so I'd like to know if you have any suggestions for 1) what investor meetups I should attend, and 2) recommendations for building my team (CPA, real estate lawyer, handyman / contractor, insurance broker, and agent (I have one but they don't seem to have much investing experience)).

Prices did seem better than DFW, but about 5 years ago when it was on my radar, I never found an area where I thought there was good balance. 

Just a thought.If PMS or escrow accounts seem like the best path, could you recommend specific tools or platforms to streamline these processes?

@Eric Chappell this software does seem pretty cool.

I’ve got 29 SFR and this seems to be quick and easy to do.

Or else reduce enough on price to deal with an eviction from an illegal unit.I don't know Chicago laws, but in NYC if you have an illegal unit, the tenant occupying it seems to have more rights than the owner does and doesn't have to pay rent... 

One thing I'm trying to do is to test different cover photos to see which ones draw a greater % of click-thrus (which seems like a reasonable thing to test).I'd like to be able to view the Airbnb stats to see, for each cover photo I test, things like what % of people click through on it.