I'm comfortable launching the spin single-handed. I plan to have the trims and halyard hooked up with the bag in the v-berth. When it comes time to launch, I'll clip it to the appropriate side and get the pole up, The sheet will be cleated with plenty of slack. Prefeed the guy from the cabintop, hoist as quickly as possible and trim - hopefully - in time to keep the chute under control. I can go fore and aft as often as necessary to keep the boat on course until I prefeed. Then, well, let's just hope I'm quick enough.
This isn't a buoy race, so getting the kite up cleanly is more important that getting it up fast.
I'm actually more concerned about jibing the pole. Main first or pole first? It will be a challenge to keep the chute full with limited control of the sheets and the helm.
I've tried "bungy-ing" the tiller without success. I was thinking a little bit of helm with the tiller locked just to weather would let me keep the boat more or less on course by moving to the high or low side as needed.
The race starts about 25 miles from my harbor, so I plan to deliver the boat the day before single-handed to get some practice in and to find what does and does not work.