I ski'd for years and years with various V-bottom boats we've owned. I was the same weight and height then as I am now, 6' 2 1/2" and 240 lbs. I singled with a World Team Comp O'Brian 72" and if any of you know what Caeser's Fountain looks like in Las Vegas, that's what it looked like when I was getting up waaaaaaaaaaay back then. You couldn't even see me for a good 5-10 seconds right after the boat took off. Then, I'd emerge like one of those super submarines that pops up out of the water in movies. My shoulders, arms and wrists would take a beating back then but I didn't care, I loved water skiing.
The last time I skii'd was decades ago and I haven't skii'd in years and years. I'd love to but, at almost 72, and not quite as strong as I once was, I think I'd yank a shoulder right out of its socket if I tried. As for a pontoon with a 150 on it, yeah, even with an aluminum prop, you should be able to get up. There's some tips and tricks that may need to be learned. Some do the "two skiis" take off then, kick a ski off once their up. Some "drag a foot" to help get up. Neither of those methods worked for me. I just muscled it out with both feet in the boots and would finally emerge like a drunken whale. My kids used to tell me a long time ago, "dad, you really move the boat around when cutting"!
Scott