Update:
At long last, I received full payment on April 21. So it was over 6 1/2 months between payments. This was very frustrating and annoying, but the good news is that I survived it.
For me, this entire experience has reinforced the importance of buying less than you can afford, and having greater reserves than you expect to need.
If this helps, here is a snapshot of this property.
10/6/2021 - Closed on home. The property was a near-turn key. I spent about 3 days fixing things myself (this is an out of state property, but I decided to go out for closing, and fix some stuff myself). New property manager walked through on 10/7. Made a list of what work needed to be completed (replace front door at my request - I loved the original door, but many hours of attempting to make it work made me realize it just needed to be replaced...sad to see it go, refinish floor in 1 bedroom, move stove, paint).
10/29/2021 - The guy in charge of my home left the company.
10/29/2021 - 1/11/2022 - Many emails exchanged regarding progress. Poor response
1/11/2022 - Email from Property Management company stating that the home is ready for marketing. They recommended renting it at $1500/month. Their photos if the home were crap. They had really ugly watermarks on the photos. Yuck. I pushed back on the rent (nothing less than $1800/month, looking for $1850).
2/23/2022 - Identified Section 8 tenant, which was my hope with this property. So begins a new journey.
March 2022 - Inspections, fixes, and reinspection. All good (whew!)
4/19/2022 - Rental amount ($1850 vs recommended $1500 from PM) approved by Chicago Housing Authority. Note: The tenant is renewing their lease, so if I went with the original suggestion, I would be out $8,400!)
4/19/2022 - Tenant takes possession. So just over 6 months from closing until tenant moves in. (note: 6 months of holding costs: mortgage, utilities, etc). Received first rental payment
5/3/2022 - Discovered work that the property management company had charged for, and that I had paid for was NOT completed.
5/26/2022 - HUGE water bill. Over $1,000 for 2 months. Turned out toilets in both bathrooms were essentially running non-stop, plus a couple of other minor issues. The usage was 101,000 gallons for the 2 month billing cycle, of which the home was only occupied for 10 days.
May - August 2022 - Many issues with the PM. Notified (per contract requirements) of intent to sever relationship.
9/23/2022 - Signed agreement with new PM
10/01/2022 - Final direct payment from CHA to me
10/23/2022 - New roof on garage by new PM. Super happy!
10/31/2022 - New PM splits off. All hell breaks loose.
11/1/2022 - 4/16/2023 - Lots of frustration, many emails, no solutions.
4/17/2023 - Payment confirmation from CHA
4/21/2023 - Received payment for all missed months.
TLDR: From date of purchase until first payment - 6 months (no income). Received 6 months payment. No payments for another 6 months (all of the missing 6 months were caught up in the end).
