Pharoah,
Mate, I am/was in the same position except I am now 38. Late last year left a job I hated (loathed actually) paying quite well, traveling extensively around Asia, and working fairly autonomously. Spent the last two years of employment wanting out, and finally it came with the decision that it was now or never, and I have NEVER looked back, not even once!
Started training full time Dec08, and should have my ATPL theory and MECIR by years end. After my next few "apprenticeship years" in the industry, I don't have to fly the biggest an the best (although I wouldn't knock it back!!), whatever comes my way, freight, airlines, corporate whatever, that is the compromise I must have to make a career from this at this time in my life.
A jet is a definite possibility, the question is when. I believe I could be reasonably well positioned if the industry improves over the next 3-5 years, only time will tell.
Don't ever look back and wonder as it really serves no purpose, make the decision that will make you happy, and go for it with everything you can...just my 2 bits worth.
Good luck with it all