Skipping the 20 part, launching off a trailer SHOULD be simply untying the boat from the ground, installing the jib, backing it down the ramp, pulling it to the dock, and putting the main up. If you stay focused, that could take 10 minutes, and no more than 20. Same thing coming in, plus some additional time to dig out the keys and go get the car. Pretty easy to winch up the trailer, even with cradles vs rollers, although someone might need to guide the bow.

As to the 20, I don't know of a single newbie couple who bought one and still sail it. If you flip, will your wife and kid laugh or cry? If they will laugh, go for it.