Am I ready to retire?

[Jean-Paul E. Gagnon]

I'm thinking about retiring (after 23 years of teaching) in June, but I'm trying to get as much advice as I can before making the leap.  My data shows I'll have $3,500/mo cash-flow in the first year.  By year two (due to increased rent and decreased expenses) that cash flow will increase to $5,500.  I like Real Estate and want to keep investing, but I'm not sure I'll be able to find lenders without W2s.  Before I get to my question, here is some financial data for me in June 2021, on the first day of retirement:

Monthly PITI for 7 Properties: $15,485

Rent for 1 lease-to-own property:               $1,643

TOTAL PITI and RENT: $17,128

-Monthly Rent collected from tenants:         $32,225

-Income from Summer truck driving

  job which I will keep doing for a few years: $2,000 ($24,000 averaged over 12 months                                                                         TOTAL INCOME: $34,225

Summary: Incoming cash is almost exactly TWICE my PITI

Credit score: 820s

So here's the question: (on a scale of 1 to 10) how likely am I to procure financing on additional properties after retirement?

1=Impossible

2= not impossible but there are no guarantees

3=Oh heck, I can find you a lender in 5 minutes!

Thank-you!