I self manage 7 units on the south side so my perspective…
1. Did you already close? If not ask the seller to provide bank statements showing on time/full rent payments. My sister in law pressed a 3 flat in cook county a year ago and the owner said all tenants paid on time and in full. They were lying and all 3 tenants had to be evicted. The process took a year and a ton of lost income. The list goes on but this is the first thing that came to mind.
2. use the Chicago Area Realitor’s Association lease. They provide here free on BP.
3. I have a good handyman, but depends on the area and the need. Also ask around the forums, lots of Chicago guys with connections.
4. I use Zillow. They screen tenants and let you upload leases to sign digitally. I have had really great luck with them and it’s only $10 a week for a listing. I have always had a tenant within two weeks.
Where is the property located?
Congrats on getting back in the game!