jjroland,

Everything is frustrating because it's new to you, you'll get the hang of it...it's a little dance to make everything work together. Making conforming clothing requires a certain process, once you've got it you are good to go.
Might I encourage you to try AutoGroupEditor, a good program for grouping. But there are many ways to group. If you model with grouping in mind then Posers group editor will work. UV Mapper Pro will group. 
But again, you need to keep in mind your grouping when you are modeling, you don't have to of course...but it does sometimes make the process a little easier.

Hope this helps.

Comitted to excellence through art.