I don't think that the squeak community is large enough for an
un-targetted bounty list to work straight off.  There aren't enough people
floating around with time on their hands but without projects of their
own...

I agree that the Google summer of code would be a much better model.

Pick a feature, find a student or programmer who would like to implement
it, collect the money.

You would need a clear understanding of who is going to do the work, a
clear timetable for the work being done and someone to monitor progress.

To give a more concrete example:

My personal wishlist for Squeak is mostly focussed around making the image
a place where I can live, rather than a nice place to visit.  One of my
needs for living in Squeak is a decent HTML renderer; either pure
smalltalk (hard) or something like KHTML wrapped as a primitive (easier).

Assuming this is the goal, the first step would be to find someone
suitably qualified and keen to implement it and to work out a suitable
payment.

We could then set up an account on a site like fundable.org where people
pledge money on the understanding that they only have to pay if enough
money is pledged and the goal is reached; or go the 'low-tech' solution
and have someone keep track of promises by email and a website.

Best wishes,

Russell
mail at russell-allen.com