1. Easy.
2. Wanted to do this, but wasn't sure how, exactly. Checksums and comparisons can take a long time to calculate; doing so could really slow the process.
3. and 8. This could be done by using system's folders. It could also save on load time, or have a truly horrendous load time when you finally do need to open a group. It'd take a bit of work either way. We'll see...
4. That could be done easily enough. Not sure why you'd want to, though.
5. That.... Probably won't happen.
6. Don't understand this one. Do you mean cut/copy the next thing each time you paste?
7. Regex replacement on groups could probably be done, especially if there's a library out to handle that.

Right now, I'm working with another project of mine, but if I ever need a break from that one, I'll implement some of these.

I'm hoping someone else comes along to pitch in. That'd make life easy, heh.
7. option: user define sets of tokens to be stripped from clip or clips in
a group. example: token_set-1 might define: *_@-<tag> whenever a
"cleanup" is initiated uses token_set-1, all asterisks, underscores,
ampersands, hyphens, tags will be stripped from the target clip or
clip-group.
8. OH! user defined objects such as clip-groups should be persistent across
sessions, even if unpopulated when clipbuddy is closed. maybe an option to
save "empty" containers across sessions - default is delete container such
as clip-group if empty when clipbuddy closes. Program option to define
save directory.