My wife owned her own 20 footer before we met, she slipped it, docked it and ran it by herself,, although the docking part was always an adventure, but never trailered.. So what I started doing is, have her back the truck, hook up the trailer, drive to the ramp, prep the boat and the whole time I just watch to make sure she does everything right,, don't know if she would do it by herself though..
now when we get to the ramp, I get in the boat, she backs me in, parks the truck I pick her up and off we go..
when me and the guys are on the jet ski's, she runs the boat no problems.
If we get the 29, I don't know if she is going to be able to take it out by herself, because she will be have problems docking it back up.