I'm aboard a 33 Morgan OI, love the boat, it's fantastic, sails very well, has lots and lots of storage space, relatively large cockpit, and the only regrets I have is not doing this many years earlier.
DON'T walk away from the pension - you'll need it. I've been saving and planning for this trip to the sunny south for more than a decade. I wish I would have made the trip a decade earlier. Now, at age 72, there are some things that are a bit too difficult to do, but fortunately, in the cruising community, there are lots of wonderful folks that are willing to help when you get in a bind. Of course, I do the same for them as well.
In contrast to others, I would NOT suggest selling everything, jumping aboard the boat and sailing off into the sunset. Instead, try living aboard for a couple weeks, then go for a couple months, etc..., and see if this is truely the lifestyle you wish. For many, it's not the way to go. It takes a lot of moxy to live aboard, and there are lots of things to consider, especially when you get older. Healthcare, good dental care, etc..., they're all very important factors to consider. For example, I cracked a tooth on the ICW in norhtern FLorida, saw a dentist in Palm Coast. Nice guy, wanted to sell me dental implants and dentures - cost $22,000. NAH! Still have the cracked tooth, but I'll baby it along until I get back to Maryland in April.
My best advice - take your time, think things over carefully, then make the decission.