Every day my team and I are making massive progress in REI and I already have the freedom to travel back and forth anytime I want.  

Arbitrage and seller financing, those 2 actions alone afford massive speed to scale. 

I agree though, an individual condo unit purchase in an old building without the ability to do or understand your due diligence adequately is a massive risk.

I am doing this completely remotely, which has been a massive pain/lesson learned (topic for another day).I signed a very high-level agreement (i.e. expectations simply say "drywall and paint") with him for drywall and paint work at my home for a total of $10KI have paid $5K as a down payment as well as ~$2K in materials over time, as neededThere have been multiple break-in's in the home, and he has done me favors of working with the police, and boarding things up.

PCP has nearly 6,000 homes, boasting a massive community of both residents and STRs.

We have a very hard core policy on smoking / vaping, screen shots below...

One downside I see to this strategy from a tax perspective: You are unable to take advantage of the STR loophole which is a massive offset of your tax liability for many folks.

Stools also might add but decided against because I didn't want it to feel cluttered Garage - I almost added a massive floor rug but was advised to not, as it was just going to get destroyed within months and I didn't want to repeat the cycle of continuously buying rugs. 

Also, Chicago is a MASSIVE MARKET .

@Brian Kloft I appreciate your reasoning here massively.