On the paint issue, how old is the paint? Is it lead based and will it need to be remediated?

Get someone with insurance!!

All the dude has to do is fall off the ladder and you will be supporting him and his family for the rest of his life.   I've seen than happen and it scares the crap out of me.

$640/square is way too much for vinyl siding.  I'd expect to pay under $400/square, and that would be for the insulated vinyl and the trim work.  That would also be insured contractors.

Originally posted by @Dirk Richmond:

..... if someone gets hurt, they're likely going to look to you. If you didn't have your workplace up to OSHA standards, and even if you did, they may try to sue you. There are a lot of hungry lawyers out there.

& in New York we have the dreaded Scaffold Law that has ruined many businesses & home owners.....take adequate precautions.

The Scaffold Law, enacted in 1885 as Labor Law 240, places almost absolute liability on contractors and property owners for gravity-related accidents at construction sites, even when the workers are at fault in part or whole.

I got two quotes from different companies for the siding. It's going to be minimum 11,000 dollars so I am definitely not doing it. Will start looking into painting instead.and yes I will be going with a professional company.

thank you for all the valuable advice everyone probably successfully steered me away from a bad decision!