I came across your post today and I wanted to share my experience and what has worked for me. In 2009 we bought a 1994 Mastercraft Prostar - best boat EVER. Anyway, I grew up on a lake and I was so mad that I couldn't get up on my favorite slalom ski - KD3000. My last boat was an I/O with only 6 cylinders and I had to hang on forever to come out of the water - lots of drag, not enough power. With our new boat, I tried for probably 6 weeks and I don't give up easily. I kept thinking that with all my attempts that eventually I'd build up enough strength not to lose the handle. My husband was still learning how to drive a boat (and more importantly, pull a skier) but it wasn't always his fault. My weight (around 205 - 210 at the time) and my "skinny" ski were the biggest issues. I also work out a lot and I'm in decent shape but for a woman, I was dragging way too much. I did all the right things about coming out of the water, but at some point you start to feel like you have forgotten how to ski! (I also was about 30 pounds lighter a few years prior and had no issues skiing, whatsoever.)
For my birthday that year, I bought myself a wider ski, I still wasn't able to hang on long enough to get up. I read all the forums and searched for answers. I must have read this somewhere, but I decided to try out our FlyHigh Ski pole that we got with our boat. It's meant for wakeboarders and if you are going to be doing some serious cutting, you wouldn't want to try this. However, even though I'm a decent intermediate slalom skier, I don't go out too far on either side of the wake and I don't cut hard.
Within a couple of attempts, I was finally able to get up. My new ski was actually purchased before my birthday and on my birthday was the day I finally got up again! (Happy birthday to me). I've also started using my ski vest that we use for show skiing (much thinner, made by Eagle) and that combination is what works for me. I can't tell you how excited I was to finally ski again. I hate skiing on 2 skis and my few attempts at dropping a ski ended up being just too dangerous for my skills.
Being a part of a ski club, I now have my own wooden ballet water ski that is quite large and I have no issue getting up with it behind the boat with the pole, but when I want to slalom, we hook the pole and I come right up every time.
I've also found that the pole works great for overweight beginner water skis on 2 skis. They might struggle with deep water starts, but put the pole on and they pop right up.
Anyway, my goal this summer is to lose 30 pounds again and get back to learning the course. I'm 45 years old by the way, so I know it's possible for you to get up and ski

Good luck and have fun!