I could commit to small amounts of money.
I could commit to larger amounts of "computer related stuff" i.e. a $100
book from Amazon. That way I can claim it as a business expense easily and
therefore can spend more.

I don't know how to manage the distribution so that people don't get their
noses out of joint.

Off the top of my head...how about a monthly prize pool voted on using
SqueakPeople? People donate money, books, etc and each month (or week, etc),
everybody votes on the enhancements that have been implemented. The best bug
fixer get a prize, the best VM mod (Tim and Andreas get all of those :), the
best new plugin, etc. It gives people some encouragement, especially
newbies.
Maybe only maintainers get to vote which would encourage people to become
maintainers.

I can see some problems with this distribution method, but maybe they can be
worked out.

Russell