However it is largely based off of relationships and working history.

But WCC Division has a history for that, just sitting back and compiling evidence until it's at epic proportions enough to be a slam-dunk and, with all the ancillary people along with.

Most S8 tenants have a history of bad decisions, often having convictions, evictions, bankruptcies, chargeoffs, collections, garnishments, etc.

I think the winter market concerns are really primarily only really worrying if you are looking at a larger SFR attracting families to due the "school year" issue - but other types of strategies I don't think its as much of a concern

Landlords would be free to take chances on irresponsible people with bad histories. 

You will be dealing with high school kids who are your employees...I know, there will be a manager, but a manager can only go so far...Plus corporate can come and make you change this or that, you will be obligated to comply.Seems like a headache to me even more than with rentalsSo Ive decided when I retire, I want to enjoy my life, not to deal with a headache from a restaurant

Show the lease agreement, show his rent payment history, and show any written evidence from the tenant that he admits to being late/unpaid.

A simple baseline plan might’ve steered him toward properties with more reliable maintenace histories or a stronger neighborhood profile, saving him a lot of sweat.

Quote from @Craig Sparling: I consider myself an old school fundamentals guys. 

They already have a track record (good or bad) with you, so you can decide based on payment history, inspections, etc.