But I’m definitely open to anything that’s within 2 hours of travel distance to the city, anything to get that cash flow!

@Landon ThompsonMost communities in Illinois prohibit an accessory habitable space in a detached garage.  

I'm trying to game-plan my way out of the things I don't particularly care to do - I've forced myself to hire plumbers to do stuff that I can do (I was a plumber while in college) just to get myself out of the habit of doing everything myself.

My agent is telling that I will not be able to get what I planned on due to recent comps, (there are only a couple recent comps) due to no finished basement, lack of a 2nd full bath, etc.My reasoning for not finishing the basement is due to time/money as I have hard money and have had the property for 6 months, and then due to the fact that the basement height is 6'8 in one are to 7', which I know for habitable space should be 7' at least. 

(I'll reinforce that point, that under the new law, you would have to live there for the second place to be considered legal as an STR.)One other option to not deal with the Airbnb law, is to rent out both as furnished 3-6 month rentals for traveling nurses.

Go out of my comfort area time/travel wise.

I'm looking to build my build and hold portfolio and both of these places are on my list to travel to and check out first hand.

You don't have to "go big or go home" with out of state investing but you'd better be sure it's makes fiscal sense once you factor in PM costs, travel costs, etc.

I'm new to Bigger Pockets, too, and I travel to Oxford for the annual William Faulkner conference, and love Oxford!  

I get to travel to our nation's biggest and best cities.