If you don't want to long-distance landlord and find it to be a pain, then sell it, 1031 exchange it or owner finance, like you mentioned.

You also have great interest rates, 2.5 to 3.5% You mentioned that you started buying them in 2013.

Red Flag #1 - Positioning: He doesn't mention anything about pricing or what his protege program is until you sign up for it, that in itself is a red flag, but the most important red flag here is the position you are put in when you sign up.

They mentioned James Kandasamy is very hands-on with operations. 

Not to mention, asbestos siding that would not have been an issue, is an issue as that also has a massive hole in it.

Every system you try will have flaws, or you may salivate over a feature that appears in other software.Some familiar names are mentioned frequently: Stessa, Apartments.com, RentRedi, TenantCloud, Innago, RentManager, Avail, Rentec Direct, Doorloop, etc.I recommend conducting thorough research on each app online to understand their offerings, pricing, etc.

I think it'll come down to (as you mentioned) buying the next deal correctly.

Why will likely determine how because if you are looking for cashflow vs. appreciation vs. quick capitalHow could it be househacking, brrrr, flip, long term -> You mentioned BRRRR, which is an awesome strategy but will only work in specific sectors of Chicagoland. finding the perfect brrrr in the current environment is extremely tough!

Might make sense to keep it if you have super low interest rate and around 2000sqft or less.Some great groups have been mentioned here, but be careful who you meet with. 

Ive heard it mentioned many times, but unfortunately,  I haven't taken the time to learn about it yet, although it is on my agenda to.