I think funding for infrastructure continuity can be put on a backburner, since Nokia has pledged its support for maemo til the end of 2012. A backup plan in the unlikely case of Nokia terminating its support earlier than 'end of 2012' wouldn't be such a bad idea, but it's something that can be setup within short notice and coordinated through other channels anyway (irc, mailing list).

As far as 'funding for development' goes, I would think offering a fixed sum of bounty for certain targets are more cost efficient with more predictability than settting some goals and paying 'mercenaries' to chase such targets and paying them hourly/daily/period fees. You'll end up having to deal with issues with:
- selection and qualification of whom to contract
- negotiating the contract (goals and schedules, milestones, late penalties, etc) with the parties
- setting budget. With lower manhour/day budget, you'll likely to end up sourcing the manpower from more limited regions of the world.

In short, it becomes a business.

Imo in this case, we should just be straightforward and say, "Hey, we're a group of N900 lovers who wish to see yet a few more years of this platform to grow by getting A, B, C components opened; whether by license/code release from the current original owner or whether they're a completely rewritten/clean reverse-engineered plug-in replacement. We've collected a donation of XXX amount and we would be glad to offer this as bounty for fulfilment of said goals. Cheers. "