Help with decision to hire a roofer as a side job

Posted this in the insurance forum but thought maybe I should do it here too… sorry for the double post!

We need a new roof on our rancher-- 2 layers, no leaks yet but our home inspector suggested we replace within a year or two of purchase and we are into our 3rd. I’ve had 5 companies come out and been able to narrow it down to 2… both master elite roofers, been in business for 15+ years, reputable, all that good stuff. Both in the $8500 range.

However, husband now has a new plan: hire a friend of his brothers… who does roofing for a living… but to hire him as a side job, saving us about half. The guy is stopping by tonight to take a look and answer my questions. After speaking at length to the other companies and doing some googling after, to see which things really do seem important to me, (30# felt vs 15#, snow country attic vents, timberline architechtural shingles, weather watch leak barriers around all the eaves-- one of my guys says it’s “code” for us to have 2 rows of this stuff, nobody else agrees, aluminum step flashing and chimney counter flashing in brown to match roof)…I have concerns as to why the cost will be half with this guy. What corners will be cut. And much more importantly, is it worth saving this money at the risk of hiring someone who will be performing this work without insurance coverage. If he falls off the roof and sues us, the cost will obviously become much greater in the long run! Not that I think it’s likely but things happen and if it were a smaller job, great. But a roof is a huge deal and I feel much more comfortable hiring a reputable company with all the necessary insurance and workers comp and all that good stuff.

Husband and I are butting heads here obviously. He is only concerned with the bottom line so it’s up to me to ask all the questions I want answers to, and most of the things I listed above are things he couldn’t care less about “this guy does roofing for a living, he will do it right and everything will be fine, stop worrying”, that sort of thing.

So I will ask the questions and see how I feel BUT my biggest question here is, would you hire someone to do a roof as a side job?

I wasn’t budging on the insurance part so husband said he verified that this roofer will sign a waiver stating that if anything happens, he won’t sue. Somehow this doesn’t settle me much as I’m sure there would be a lot of loopholes if indeed something did happen, and I’m not sure this little waiver we type up would be sufficient.

Anyone have any insight to offer here? I’d be very greatly appreciative…

Thanks very much in advance,
Nicole