@Jeffrey Bourque This is where the "art" of the deal becomes more important than the "science"/numbers.

MOST IMPORTANT - this requires level 10 effort. master the art of finding great tenants.

Set on 3.3 acres, this home has everything your buyers are looking for: a brand-new septic system, a state-of-the-art wall-hung boiler with radiant heat, and a stunning new kitchen complete with updated appliances and an island for gathering.

Collecting rents is an art and a science.What you should depends on where they are with their late rents.

Sounds like you’ve mastered the art of adapting and following the right people when they move.It’s crazy how a buyout can flip everything overnight—14 years of loyalty, gone just like that.

This has the obvious weakness of the unknown nature of future cap rates, but that's really the heart of your question here.Estimating future cap rate is part art, part science. 

Credit analysis and underwriting are as much art as science. 

@Brian King If/when you're ready for a small MF, would something like this "float your boat", https://www.realtor.com/realestateandhomes-detail/1710-Liber...?

Looking to learn more about seller financing, the art of the deal as well as connecting with like minded investors in Chicago and beyond!

The city itself is established, older neighborhoods, better city amenities (museums, arts/music etc), more pro sports, more hills, bigger river, has a streetcar, arguably better nightlife overall.