[ScrimpAndSail]

Hi Every one
I guess I need to start with my situation, needs, & wants.
I'm new to sailing. It's been an interest on and off since I was in my teens. I'm now in full-on midlife crisis. Work is a horrible travisty of all that's holy on a daily basis. I can't emphasize this enough. I don't want to reach the end of my life in a house full of junk & no life experience. I never went to college. (At least for a full degree or even close to it, Just what interested me. I could never discover a course of study I could stomach that would be worth while economically.) None the less my job has decent pay for someone without a college background. My soul is left dying.
Bad Timing- I know, But I'm almost ready to sell my house for less than I could If I just could wait a few years. This will only allow for a very well priced older boat. Maybe 20,000 or so.
I know, I know. Sweat equity OK, but it has to float.
I'm Taking classes to learn to sail. I just wouldn't feel comfortable without a foundation to grow on. But here is what I need-

Rig- About the simplest rigging for a single hander. I'm single, I need to be able to sail it independantly. I don't want sailing to be a struggle. Being able to reef in a hurry is important for safety's sake. I'd rather not die of procrastination. Remember, I'm still an inexperienced neophite. I've read a bit, But hands on is still a work in progress. The Cat Ketch seems to get good marks. So does a fractional Bermuda Rig. The Junk sounds good. Especially with reguard to maintenace costs. Something that will always likely be the real struggle. Speed is nice & the CK & FB sail to windward better. Speed is not the most important factor, Safety, Ease of singlehanding, & Cost of maintenace are. Also, Older Junks are few & far between.

Use- While I'd love to sail around the world & Not in race fashion. It would be a great personal acheivement. In practice I veiw cruising as going from place to place, not a distance goal. I would start by Island hoping the caribbean. Also, I just can't seem to shake the need to Island hop the south pacific. While I definately want to see the caribbean. There's really are limited number of islands. The islands of the south pacific are nearly innumerable. This means blue water from the caribbean to the south pacific. Also, I don't want to be forever parted from the US. I'll need to make that jouney from time to time. This means multiple blue water travels. Also, It's important to note- The Islands of the south pacific have extensive reefs with very shallow waters surrounding them. 10 more feet away from shore & your in blue water. These are under water mountian peaks with the tops capped by islands. This makes the versitility of the boat very impotant. Swing keels seem doudtful as they come with their own problems. Damage potential, Cost of maintenance, & also Far & few between among the used beauties out there. This on top of the need for a boat that also meets the rigging requirements.

Size- We all like room to move about. I'm single but not forever. The boat will be my home. I need it to be comfortable as a liveaboard. Small size is a bonus for both initial cost & maintenence cost, But I do need to live. Don't forget that my Blue water travels will only be to get to the next stop or area, not my life mission. I would like to make passages as safely as possible. But if I can't go from island to Island & mysterious shore to shore, Why Cruise?!

Hailing all those that would chime in. With all the above in mind, What would be my best reletively common choices out there that would meet these needs? And also, What would be the pros & cons of each choice?

If I've left anything unclear, Just ask.