Thank you all for your replies.
Here are some answers to your questions.
1) we don't have a catbox, but we do have a 1ft diam, 12ft long tube that is attached to the trailer. We keep the sails, fenders, rudder stick in there.
2) mmiller, we learned to rig the hobie using that video.
3) When discussing boat storage we didn't specify mast up/down; we just asked if we could keep a boat parked there.
3b) We have not yet tried asking about a parking space for a boat; will pursue this.
4) Would like to rent a space on shore from a private party, yes. We've been working on trying to meet more people to broach the subject. Not courageous enough to post a craiglist ad yet, but we'll see.
5) We live in Maine, and out nearest water access is Searsport, ME. If we need protection from the wind, we launch at Stockton Springs, ME.
6) Raising the mast is very difficult for us. There aren't beaches here to park the boat on, so we have to do it on the trailer. On the beach we can hand raise it, but on the trailer we aren't strong enough. We use a winch on the trailer to assist, but it is so dangerous that it takes us a while to go through our safety checklist. We dropped the mast once (the link pin wasn't in) and it almost hit my father and several bystander children. Most of the boat launches here are busy and have very little room for setup (due to overhead power lines), so we are often forced to raise the mast on the launch ramp.
7) We follow Matt's video for rigging, but almost always have to do this on the water. We spend a considerable amount of time trying to get the boat positioned into the wind. We still have considerable difficulty raising the mainsail.
we have improved rigging time by adding quick shackles to the jib and the block-and-tackle to boom.
9) I'll try to estimate the time we spend on various tasks:
-Picking up the trailer and driving to the coast: 70-80 minutes including trailer safety checklist
-Disassembling the trailer ties, and preparing the stays/mast for raising: 30 minutes
-Raising the mast (including safety checklist): 15 minutes
-Applying sunscreen and changing into wetsuits: 20 minutes
-Getting and eating food: 20-30 minutes (This is usually necessary because the entire process takes so long. if we could shorten it, we won't need to eat in the middle)
-tying fenders up: 10 minutes (working on getting quick shackles for these)
-Final gear check, gear attachment to boat: 20 minutes. (we reorganized our system last month so that most gear stays in the same drybag/bin all the time. This used to take much longer. we're also working on various means of quickshackling the gear to the boat).
-Raising the sails: 15-20 minutes
10) what we use to secure the boat on the catHauler trailer: about 20 tarp-bungees for stays, two ratchet straps for hulls (reduced from 4 for time reduction), mast is secured by winch at front, and by block & tackle at back.
11) typical "gear" that we take in three or more dry bags: spare paddle, warm dry clothes bag ICoE. emergency phanny pack with neoprene gloves and hood, snacks, 4L water, clothing needed for today's weather, marine radio, high lumen flashlight (in case of night sailing), two lifeJackets, two throwable pfd squares, 3 fenders, boat tool bag, 1st aid kit, depth charts, cell phones, 15lb navy anchor, three sets of 3/8" rope.
I'll post our checklists and a photograph of the ready-for-trailering setup for reference.