One thing I was wondering is, do you have any old postings about how to go about getting road gigs?
Nope, haven't written about that before. For the road gigs I do, I usually have a fellow comic from that town (e.g. Boston, Chicago, or D.C.) who knows I'm decent put in a word for me at the good show(s) in his/her hometown. If more followup is needed, I'll send along an email with a brief bio and a link to a set online. That usually works. Then I go to the show and try to kick ass so 1) the comic that referred me doesn't look bad and 2) I can get booked again there.
One way being from NYC helps: Audiences here are as tough as they get. To paraphrase ol' blue eyes, if you can make 'em laugh here, you can make 'em laugh anywhere. (Well, unless your jokes are all about riding the subway and how dumb people in the south are.)
So if you show up and have a great set, you can prob get booked again pretty easily. But if you're not confident about your ability to do that, it might be a better idea to hold off before getting out there. You don't want to do a shitty set and wind up blacklisted from the place.
Other comics I know have actually set up their own tours which is a cool, DIY way to go about it if you're willing to put in the time to set all that up. From what I've heard, these shows can be pretty hit or miss though.
Of course, if you have an agent, they can set up shows for you. But that's a whole different can of worms...