First off, you're a lucky son of a gun!
You wouldn't think diapering someone would be so hard, but i know exactly what you mean. I've only gotten to diaper two girls in real life (both times we met online, and then met for only one weekend), and both times I was horrible at changing them.
Watched quite a few video clips, and one popular method is doing the second tapes first and then the bottom tapes and the top tapes last.
CVS makes a refastenable "pull-on" diaper, but it's really a normal diaper with one big tape on each side so it's real easy to put on. However it has that cloth-like cover and it doesn't hold a lot. Suggest getting plastic or rubber pants if you go with them.