We have a 27' Kodiak. I am totally new to RV'ing and I can easily hitch solo. We have an F150 with backup camera. That helps me line up, but I do get out when I am close to eyeball the hitch. It usually takes me a couple of moves to get correctly lined up then the TT drops right on the ball and I can lock the hitch. We have WD bars. They are no big deal for me. I can get them on in a minute or two including the anti-sway.
Of all the things I have had to learn, hitching up is the easiest. I do worry about sway, but so far only a couple of adventures in mountain passes with high cross winds have made me go white knuckle. I just slow down. As of now we have 5 trips and 1500 miles. I have driven half. My wife is experienced with RV's and has been a big help. Backing into sites and my home parking place is much easier than I thought it would be. I still do a bit more forward and back than I probably need, but by and large I am comfortable with hitching up and towing alone. This surprises me since I have less than 50 hours at the wheel.