Update: I spoke with one solar company and their proposal, which includes a new roof. At this point, I was almost 100% decided not to go with the first guy as there were a few small but significant red flags, in particular, no breakdown of the new roof cost, and some weird energy estimation charts.
Speaking with the second solar company, which doesn't do new roofs itself but partners with an actual roofing company. The roofing guy stopped by yesterday to do a very detailed inspection of the roof and attic, and found and showed me a few small leaks already. We discussed a metal roof as well, but it doesn't seem like it would make sense to us to go that way. Guy is highly certified and seems like he really knows his only job - to do roofs.
His proposal will likely cost more than the first guy's, but I feel it's worth doing for many reasons.
Still pending to see the actual proposal from the second solar company, will update later.