If you don't foresee any major obstacles to qualification, I'd be happy to set up a viewing for you.

STRs need to be viewed from a 365 day lens so if the numbers work well then, you still can be successful.

One property is 4655 Royal View Dr. and the other is 3082 Parker Rd..

Ideally, my dream is to have a condo in my favorite neighborhood of Chicago (Lake View).I'm 24 years old.

It could even be (more) interesting from a lifestyle point of view as you'll get to stay in different cities/houses every time you go.

It will give you a 30,000 feet view of real estate investing as a whole for different strategies and will allow you to find new ideas and to explore and see what works for you!

I'd like the building to be within 10 minutes walking distance from a Brown Line L stop, ideally in Lake View, North Center, or Ravenswood.

However, I don't know from a practical point of view if it's doable 2) Condo vs townhouse vs cashflow: I noticed condos  and townhouses are way cheaper in fort myers FL ( however risk of hurricanes) and maybe more opportunity for cash flow.

Sorry for the long winded back story, but end game is to put a A frame on the existing 20x40' stem wall above near where I"m standing, and put some stairs into a drop down area below for chairs/fire-pit overlooking the river canyon below (but out of view) under where the drone is flying.

OTM = General, overhead/widescreen view of nationwide market tends.BPRE = Detailed ways specific people are making money in real estate.