I was once in a simular situation. I took a weekend sailing class, and bought an old Laser, (like a sunfish), for $500.00. After a few weekends on the
water I knew enough to be dangerous.
I just moved up to a
trailer sailer, and I'm still dangerous, but I have a good idea where to go from here. And every weekend the
mast and
sails go up easier, and easier.
The tacks, and gybes go smoother, and I get better at
steering, and setting and balancing the
sails to get where I want to go.
IN a couple of years I'm going to move up to a 30-40ft cruiser, ( I still don't know the exact
boat, but I'm narrowing down the list, and writing down must haves).
If you want to go down the same road, so far it is working out good for me. I have decades of
experience of large
power boats, but sailing a small craft takes a completly different mindset.
I would recommend the same, get a small sailboat, and sail the heck out of it. In a couple of years you will have answered your own questions.
I
sold the Laser several years lator for the same
price I paid for it, and except for a few small
repairs, (less than 20 bucks), I essentially sailed it for free.
At that
price you won't have a heart attack, if you bang a
dock, or run aground. Also in a big mistake, you just climb out, and drag the
boat back to
safety, can be easily singlehanded, if fact it is kinda mandatory.
AND the boat punishes your
mistakes intantly, so you either learn fast, or get to sail around with mud stains on the top 3ft of your
mainsail. Either way it's all good. Welcome to CF.