+1 to NYC. I tend to avoid selling stuff on CL because I don't want to directly deal with the potentially creepy person that actually wants my stuff. I guess what I want is a minimal middleman that brings an extra degree of safety and convenience to the exchange.
It is a cool idea but seems to have serious scalability concerns. One truck can only hold so many items, you'll need drivers with CDL endorsements, insurance, fuel, etc. for every truck you add.
He doesn't even know if it's profitable yet and you're already worrying about scalability?
Make a profit first. Once there's profit, a whole lot of problems become much easier to solve.
you don't need a CDL to drive a zipvan and they have a decent amount of space. They also include insurance and fuel although I haven't reread the TOS with this plan in mind, I think it might be acceptable.
OP if you want to get this going in manhattan get in touch.