Tom is definitely in a unique and enviable position among his podcasting peers in that he can start a professional venture from scratch and reasonably expect to have a sizable audience from the get-go. I mean, a lot of people, myself included, would just pay to listen to a podcast solely dedicated to Vance droning out reviews of prog rock albums. That said, getting people to pay for something they once got for free is a tough proposition, even if it is just a few bucks. I wouldn't expect that Tom will become a millionaire off the new incarnation of the show, but I have to believe that he'd make enough to get by and then some.
I don't know if Kickstarter is the way to go or not. I don't know that Tom would need it or its inherent headaches. It seems like if he were willing to invest up front in a solid platform for the show, making sure he didn't get any surprises with regards to the tech stuff (failing applications, flaky paid services, bandwidth overload, etc.) he'd basically be ready to go once he set up some kind of subscription or other payment method. The dedicated FOTs would tune in and continue to spread word of the show. I mean, what do I know, but it doesn't seem like it needs to be more complicated than that. If he gets things going within the next few months, he should be able to carry over a goodly chunk of his WFMU listeners.
It'll be interesting to see how the show becoming monetised changes things. I don't think it'll change things for the worse, really, but it will make the show different. And unshackling the show from the radio gives Tom and Jon a lot of new options regarding how it is presented. It's scary and it's exciting!