As it relates to the irresponsibility of student tenants, do you proactively visit your units once every quarter, or every six months, to get an assessment of the units' condition? 

If it’s a larger or commercial property, consider conducting an environmental check to assess potential risks like contamination or flooding.It’s also important to request a full property disclosure from the seller, which may include known issues or defects with the property.

Also, I know those who’ve gotten hit with special assessments that wiped away cash flow and some. 

Regarding Chicago, the 2024 property tax re-assessment in Cook County should cause some inventory to hit the market, specifically on the mixed-use and multi-family side of things which will be hit especially hard.

Put out a post on FB, FB marketplace, and craigslist.

College STRs are a great idea if you want something small, but I would look for small 2 bedroom SFH over condos just to avoid the potential assessments and condo captains (HOAs).

This is what Wall Street does to deploy tens of millions into a marketplace quickly. 

After going to the board of equalization to reconsider the value of the property, the came back with a updated assessed value of $8,000 and some change.

It won’t be possible to assess the damage as wires and wood are behind the wall.

Condos have a lower price entry point, but many are facing insurance assessments due to rising insurance costs, so that has to be reviewed carefully, but single family homes are seeing the same rate pressure unless very new construction.