I bought a 14 turbo about six months ago and taught myself to rig and sail it. Here's what I've learned and recommend:
The boat is like a motorcycle, fast and lots of fun, yet easy to get in trouble. It's very weight sensitive - if you don't move to counterbalance the tipping moment of the sails it will capsize in seconds. I managed to do that in moderate winds more than once.
Sailing solo means you'll need a means to call for help when you inevitably go over. Buy a waterproof container for your cell phone and keys that can be latched to your PFD or tramp.
Stay away from bridges, esp. in light winds. Tidal currents can be strong. If you get pushed under, this is an especially unpleasant way to capsize.
Stepping the mast is risky if done alone. The hardest part is getting it up on your shoulder. Watch the Youtube videos for hints. Bouncing it helps. Use a line attached to the jibstay, looped around a trailer and secured to the cleat at the mast base. This way you can reach down with one hand to grab the line while holding the mast up with the other, draw the line tight to temporarily secure the mast, then step down to pin the jibstay to the bridles/jib spool. The whole process is easier when done off the trailer.
Lowering the mast can also be a challenge. The mast base will break where the pin passes thru if the mast isn't lowered gently and directly aft. The base doesn't have enough cast aluminum material to withstand much force, but it's easily replaced with a couple of rivets.
Join a club where there are other sailors to help you with everything. Preferably join one that offers mast-up dry storage. It'll save you at least an hour per outing.
1985 Hobie 14T
2014 Hobie T2
Last edited by John from Tampa on Mon Dec 08, 2014 4:46 pm, edited 1 time in total.