I mean, I would assume that someone who doesn’t get a new enough car doesn’t have enough money to pay for commercial insurance. Also offering people rides on the street is a bad idea (because you can get robbed) and possibly illegal. This is just running an unlicensed taxi service. Gypsy cabs have been around for hundreds of years. It’s not a good idea.
Yes you do. Your bank account is in the old business’s name, and any lines of credit you have will be in that business’s name as well. Doing anything for a new business is harder than for an established one. Once you explain “oh yeah I did own that one, I just changed the name for tax purposes” you sound like a scammer.
Banks and suppliers (good ones) are not going to waste their time figuring out your scheme. They will just drop you.