My first boat was a Hobie 16. I learned how to sail on that boat. I was 15 years old and 135#s and I could yank it off the trailer, raise the mast, drag it to the water's edge, and go sailing- all by myself.
Raising the mast is no big deal if you have two arms and two legs. Face the boat downhill if possible, hook the mast to the mast-step and put the bearing in place. Stand at the rear of the trampoline and lift the mast up over your head, then walk the mast forwards and up. Since the boat is leaning downhill the mast is also leaning downhill, against the sidestays. While you're leaning against the mast, untie the forestay. Then walk it to the bridle, being careful not to rock the boat.
The other method mentioned above is also excellent and is a must if you are raising the mast on level ground. Run the main halyard through the forestay bridle and leave the bitter end on the trampoline. When you've raised the mast, take all the slack out of this line and cleat it off securely. Then untie the forestay and attach it to the bridle. Uncleat the main halyard and pull up your sails.
On sailing the H16 solo: On a boat that can be sailed unirig with two reefs in the mainsail, what are you worried about? I once sailed my H16 with one reef and no jib in a very stiff breeze and felt underpowered. Actually, I was downright bored. If you don't have to be on the trapeze to keep both hulls in the water you don't need to reduce sail area. About the time your sailing a reach with the main and jib traveled all the way out and your butt out on the trapeze is the only thing keeping that boat level... then you should think about dousing the jib. But in those conditions it'll probably be easier to reef the main than dance on the bows anyhow, and keeping the jib up just makes tacking so much easier.
The cardinal rule of soloing a H16 is pretty simple. If you're not sailing off a sandy lee shore, don't capsize. Don't fly the hull more than a foot out of the water, pay attention to the wind and the waves, and sail conservatively. On a day when you are sailing off a sandy lee shore and there are no currents waiting to carry you out to sea, get about 100 yards out and capsize the boat and have a go at righting it. If you can't, no big deal, drift to the beach and right it there.
If your girlfriend doesn't want to go sailing with you, pick up someone (preferably a good-looking female who likes boats because of the opportunity to sunbathe topless) who can play the role of intelligent ballast (and eye-candy) for the day. Get phone-numbers and make a list of potential crew.
It took me all of 9 months to outgrow my H16, so when I 16 years old I bought a G-Cat 5.7M (18'8" long with a 28' mast and dual trampolines). I still spent most of my time sailing solo, and I could still raise the mast and (using Cat-Trax because G-Cats don't drag worth a damn) move the boat to the water's edge alone. I'm 22 years old an 145#s now and I still have that boat. I still sail it solo and I just don't push it near capsize unless I'm off a sandy lee shore. Actually, it's been 2.5 years since I've capsize this boat while soloing, and that's not to say I haven't come close any number of times. I'm looking at adding a righting pole so I don't have to worry about it anymore.
