If we're talking about a muscular person with plenty of upper body strength, no problems, if we're talking about anyone without much upper body strength, they may find it difficult. The best bet is to go to an outfitter and try the skirt on the boat your gonna use it on. I don't have any problems getting it on or off of my Super Fun.
That being said .... There was a thread about getting out of your boat without using your hands a few days ago. On the Ocoee, at the takeout last Sunday, I tried this just to see if I could do it. I managed to get out without my hands but it was quite a struggle. The skirt held on real well until I could work my legs into the seat and really push out. I thought I had slipped out of the skirt but it finally came off the cockpit. Just FYI. :-)
I have had this skirt for about 5 years and only this month covered a few spots with Aquaseal: 2 small tears and a rough spot. the Kevlar rim is holding up great.