Can we say MID-LIFE CRISIS?
Yeah, I'm right there with you. I'm going through some of the same pains. Like you I just found that touring might be a fun thing to do. As I've expressed before, I started cycling again because of my health and it's bloomed into a fairly important part of my life. I'm riding more and not just for pleasure. Even though my commute is too long to cycle, (40 mi x2) I try to get on my bike, or at least an indoor exercise bike as much as possible. Even if it's for errands. I'm working on getting stronger and am venturing out a little bit more each weekend.
Unlike you, I am tied down here with wife, child and a mortgage. My wife doesn't work because of a disability, so I am truly the only bread winner. I build scenery for Broadway in a job that is technically a "day labor" job, but because of the position, it's a very steady job. If I don't work, I don't get paid. We are union, so we do get some vacation pay, health insurance, a retirement plan (for now) and other similar benefits.
Basically this all combined precludes me from extended touring. I am finding rides on the internet, to do on my own, but plan on getting involved with the Bicycle Touring Club of North Jersey. They do rides most weekends and various events during the year. Once I have a day available, I'm going to make the plunge. I figure that it's a good way to test the waters. REI also schedules rides that you want to look into. They're now in Manhattan, so it should be easy for you to get there. They did a ride along the East Coast Greenway a few weeks ago that I couldn't make, but will plan to do if they do it again. I guess my point is that you can find rides fairly easy a short distance from where you live. Even Google now has bike path information that you can access. Explore those first. A cross country trip is a major undertaking no matter what. Save that as a special treat.
I would be VERY careful about jumping in the deep end before you check things out. It's ruined many people before and will do so again. Just be smart about it. When I started to get feelings of unrest and needing to change, I looked up "mid-life crisis" online as a lark and actually found many good pages on it. It is a natural part of everyone's lives. Just about all the sites said to be very careful making major changes to your life. This is a time that you try many different things and some work but most don't. It can backfire badly. Try things, get involved with clubs etc, and find something that works for you. Don't get in a situation that you can't back out from. If the job situation changes, great, but don't just get frustrated and walk away from a decent job.
It sounds like you get excellent benefits from your company. Use them. There are plenty of rides that you can do within your six week allowance from week long rides that you can do several times a year to full six week adventures. If your company will let you take that much time off in one fell swoop. Take your sabatical and see how you really feel about touring, living frugally, not interacting with coworkers, etc. Then make a descision. Remember that it's easier to get a job if you have a job. That is especially important in this economy. You might have to suck it up, but the bean counters can't stop you from day dreaming!
Also, work on your marriage. Get a counselor if you need to. Riding away from it might end up being a bad mistake. I work in an industry that has a divorce rate second only to police and firefighters. A divorce can be very sticky and leave you in a worse position than you are now. How are you going to pay the required alimony based on the job you are in now when you are working part time and touring the rest of the time? Judges don't care about you doing what you want to do. Especially when you are on the male side of divorce. I have friends on both sides of the Hudson who ran into that problem. One lost his truck, and another lost everything except the clothes on his back.
We went through a turbulent period a little bit ago, but in finding our own interests and supporting each other in theirs, we've bridged the gap that was between us and are both enjoying life much more. Instead of hating it, work is has become merely an annoyance until I can leave. Every so often, there is something very interesting that comes my way and work is actually fun.
My wife is neither interested in biking, nor touring/camping, but she's glad to let me do it. She says that I come home much more relaxed and invigorated afterward. Try a change of pace first before you jump in full time.
Good luck with your decision.
"Most men lead lives of quiet desperation" -Henry David Thoreau
(Me, I say screw desperation. Enjoy the life you got. If you don't, find out how you can.)