I get FinTech is a high-risk activity, but imagine the industry will consolidate to one or a few strong players.

Prices remain relatively low, but appreciation may be slower.Monroe: A mix of cash flow and appreciation potential, Monroe has become a popular choice for investors, especially in areas where new developments are popping up.Appreciation-Focused NeighborhoodsBallantyne: A well-established area with high demand, Ballantyne offers excellent long-term appreciation potential, though cash flow opportunities may be limited.South End: A booming urban hub with a vibrant retail and restaurant scene.

While this is a great and highly motivating goal, most people are either clueless or incorrect in their belief as to what is required to obtain this “lifestyle”.Understanding of the “how to” get there is further obscured by the misleading, and often patently false “pathways” sold by real estate educational MARKETING companies as workshops, upsold to association memberships, upsold to mentorships.

I am in Florida and we have a strong STR market and most of my buyers bought at high rates and using AirDNA we were pretty spot on for the numbers and we were successful in being profitable.  

Section 8 is best used as a risk mitigation tool for properties in super low income, high crime areas.

By targeting better locations, leveraging Section 8 for consistent cash flow, and balancing low acquisition costs with high guaranteed rents, you've achieved impressive results like $1,100 in net cash flow on a single property.

If pool in ground is not an option or not in your budget, a quality above ground one could be a good route to go.I would definitely make sure you have an appropriate coverage.

@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

Your credit score is high enough to get something done, but whether or not that delinquency will fly is going to depend on the lender/underwriter.

However, turnover is high, probably because privacy is hard to come by.