If you could convince a bank that it is worth $325k today and get a mortgage of $245 then you could write a four year lease with his full four years being paid up front (depending on laws, maybe you could even write it in a way that it is non-refundable if he decides to move early - or at least that he needs to give you 6 month notice)- then you have that cash to use for your payments and some extra that you could use for short term investments.

. -$1,600 surprise water bill from the city after they’ve sent notices about a potential leak. 

We are in Iowa and I have noticed the market is different by state. 

There is a 60 day notice clause or the lease will extend for another year.As they left on the 2nd of the month, gave me 1 day notice, didn't finish the lease, wouldn't be okay to keep the security deposit and last month rent?

So, I would send the Tenant notice, citing the lease clause, and give them a timeline (if not defined in the lease) for completing repairs and/or restoring the property to it's normal condition. 

That is just plain rude to the tenant who planned on moving, gave notice, getting things ready in their home etc....so, don't do that.  

I’d give them notice asap.

Depending on your location, notices need to be delivered and filed with the county within certain time frames.

I got 30 days to notice my tenants of four years are moving out.

Feel free to message me and I can frwd all the 2021 docs to keep compliant.Make sure you collect a security deposit (normally I would not recommend security deposits in chicago) as the roommates tend to just move out with no notice otherwise, even in the class A areas.