As a comparison, I singlehand my HT all the time in the summer when its light, usually under 12 and pretty steady. Flying the spin by myself is fantastic. I can right it by myself with a righting pole and I carry a water bag for backup.

The HT mast is a foot longer than the i20 and the sail area is about the same, so the righting effort is about the same as the i20. I'm 200lbs.

Tyler Burd's Red i20 (he sold it recently, was Struble's at one time) had a custom trailer with long wood planks instead of cradles, the trailer was very low and the boat slid easily off the trailer onto the wheels. That boat was the easiest to get off a trailer as compared to any boat I've sailed.

I think its do-able if you are careful, rig a righting pole, carry a water bag and some sort of communication device and have a launch area with a hard pack or small hill.

It wouldnt be my first choice if it lived on a trailor and I had to rig it solo each time I went sailing.