I'll try to ride this one out.

I've been interested in Real Estate since I was a kid after riding around with my mom and our then Real Estate agent when my mother purchased our first home. 

Your goal will be to get to the point of liquidating before a market down turn or have the time to ride it out back to positive appreciation.

Otherwise, I usually rent and ride.

That timing may line up with a downturn and you will be forced to sell (no input on decision), whereas for buy-and-hold you have the option to ride it out. 

So I guess I'm back to doing the old fashioned way. 

I️ hope that plumber isn’t taking you for a ride.

I think the fact that it is a 15-20 minute train ride to the loop certainly gives it gentrification potential, but I don't feel like it really has yet...there is still a lot of rift raft that runs that neighborhood at night. 

I plan on doing my first property in the fashion of purchasing my first home (using FHA programs if needed).I plan on getting one that needs a little bit of work or has some room for improvement, but isn't totally destroyed by any means. 

Most likely facing a 20% down payment, I would almost have to do the BRRRR method to recoup my funds because the $50,000 that I can scrape up, I would want to repay back in a relatively timely fashion.