There is a lot of good information being thrown around out there. When I was in my mid teens I spent a lot of time racing sailboats. You will learn more stuff about sailing by racing with an experienced crew. Eventually I had worked my way through every position on the boats I raced on. I was a trimmer, spinnaker trimmer, bow man, mast man, and I did some helming. I have forgotten some of the stuff I learned back then when it comes to tweeking sails, but I am a cruiser now and I am not always trying to squeeze that .10 extra knot out of the boat by tweeking a halyard or other sailing control.
Start small. Sailing a dingy is forgiving and gives you valuable skills. You can sometimes rent dingys and sail them for a while to get comfortable on them. I learned on a sunfish and it was a great teacher and a lot of fun. Start in lighter winds and then do more sailing in bigger winds.
When you get to your first cruising boat go to a medium sized boat, 22-27 feet. You may find that you like that sized boat because there are some unique options that you have there. Being able to trailer a boat can be nice and it can save maintenance costs. Remember that what-ever you get the bigger it is the more it will cost. Not just the initial cost, but the cost in maintenance (I would suggest looking at the typical maintenance of a boat before purchase too because this can be expensive).
Once you sail your cruiser for a few times, find a close by place to do an overnight.
By taking small steps it should help you out.