Hello Chuck from Idaho,
I have raced and cruised many different boats, inshore and offshore, lived aboard a few (even in winter) and still get a kick out hearing how people got "hooked".
Some of the best sailing adventures I ever had included camp cruising the Maine coast in a FoldBoat, a collapsable canvas kayak with a lateen sail and leeboards. My Dad started me out in a flat bottom, leaky old skiff with a lug rig. At 8 years old I was captain of all the lake (Dad was never too far away).
My thoughts for you are these:
Always keep the fun to dollar ratio in proper balance. Bigger isn't necessarily better. Sailing a small boat is certainly more demanding and challenging than sailing a heavy keel boat. And you can go places the bigger boats can't.
Learn to fix EVERYTHING yourself. You will not only save big bucks, but you will be a safer, more competent sailor.
Keep it simple. Don't have anything aboard you cannot either fix yourself or live without.
Don't sail into any place that you can't eventually sail yourself out of. Engines can be wonderful things, but you should never trust your safety to one.
Learn to anchor........Practice in challenging situations. The ability to set an anchor, to know where to anchor and where not to, will extend your life.
Avoid marine retailers. The magazines and catalogs are all designed to lure you into spending money on things you don't need. I am not a luddite nor a a technophobe. There have been some wonderful advances in sailing technology. The marketeers will make you believe you must have all of it. Watch the people who handle their boats with real skill and who, when they are dockside, are working on their boats. Chances are, they can and will gladly steer you into making wise investments.
Sailors tend to be a friendly bunch. Show up on the docks on race day, ready to go, with a smile, a willing attitude and an honest desire to learn and you'll very likely find a ride. Do that enough times and word will get around. You will find yourself in demand. You will learn more that way than in a million years of sailing school. And you will make some great friends.
Best of luck in pursuing your adventures. And if long distance cruising is in your future, go sooner rather than later.