If you will send me a list of your "must" haves, we will find those properties, screen the seller and negotiate the deal.

They offer flat 99/mo management full service management for single families which is nice when you have a 120k investment producing 1300+/mo.Feel free to message me if you want to chat more in depth.

It's a flat 2 points for 6 month extension there isn't a monthly extension fee such that you pay extra each month?

Print it off, study it, highlight it, and keep it handy for reference.At the bare minimum, you should know:How to determine market rent for your unitsHow to set rental criteriaHow to screen applicationsState law regarding due dates, late fees, and the eviction processHow to handle late rent professionallyHow to evict a tenant for non-paymentHow to get rid of a problem tenantYou could easily read those two books, study your state law, and then develop WRITTEN procedures for handling these issues within a month.

The building is a 1900's  3 flat located in Chicago north side.

The issue is, how do you screen for cleanliness?

I am looking at multi family (2-3 flats).

Maybe from a builders association or rental association, or just individual landlords as interested parties joining together as a formal cooperative to manage their properties, provide shared resources, screen tenants and mitigate issues among other things?

I'd suspect that Cozy's primary drivers of revenue are - minimal interest made during that hold time, people paying for faster transfers, the tenant insurance they offer, and the tenant screening services they offer.And then there is that eventually switch-flip that surely is going to happen when they hit a critical mass. 

Have you thought about looking into any 4 flats?