I'm not in your area so I can't help much, but I have a couple suggestions. First, poling a skiff is not something you will be really good at the first time you try it. Fly fishing is a "team sport" and both guys have to be good at their jobs to get fish to the boat. Watch some videos online about how to pole a skiff (search on youtube, "Fundamentals of Poling a Skiff"). There is a reason you pay guides to do this - it's not just renting a boat and knowing the spots.
A good "pusher man" will propel the skiff and stop/turn it so the guy on the bow can take shots, and will be good at spotting fish- all while keeping the pole out of the way of fly line, keeping mud and bottom crud out of the boat, etc.
There are friendly people on here and in your local fly/tackle shop. Hang out there, make friends, be a good customer, and I'm sure you'll find someone to show you the ropes, or someone who is a newbie too but maybe has their own skiff. Then you can learn together.
You could also hire a guide and learn what it takes by noting what he does for you. Good luck!
