Give yourself credit for getting out there - it's the only way to get the experience you need. Also, give yourself credit for being flexible enough to change your plans when the good weather goes AWOL - I've done 3 days in the rain a few times, and suffice it to say that I don't feel any need to do so nowadays.
I still have days that seem to be uphill both ways - but there's always something that makes it worthwhile, just like your trip.
Don't get too discouraged at this point - it's all part of learning. There's no real way to shortcut the process, though asking questions here and reading some books will smooth the way a bit.
If you're looking for easier terrain, with better (more plentiful) water, there are two places closer to you that I'd recommend: Mammoth Cave National Park, and the Red River Gorge (southeast of Lexington; there's another thread active on it now.) The Gorge has some spectacular scenery, and is well known (which also means crowded on weekends.) I know Mammoth Cave sounds counterintuitive, but in addition to the cavern, it also has a very nice backcountry. No spectacular scenery, but pretty. Weekend trips to either place give you a chance to work out the technical stuff. Both places offer loop opportunities, too.
Good luck, and keep us posted on your progress.