Yes, in the scheme of things $250k is not a lot but it is nevertheless a gamble.
Trevor is indeed one of those individuals. The core issue with his approach, and I have stated this before, is that he was too conservative. A product like the X1000 needed more. Products are like fire, and money is like oxygen; You don't feed it enough oxygen and you get a slow burn. Though I'm sure if he had the millions to spare he would have put them in and we would have seen a more rapid development of hardware and software.
If I had a spare $250k I would certainly do it. I'd use Kickstarter to make sure there's enough interest; Reduces the risk somewhat.
If you were serious about this then I would join you in a heartbeat.
I don't have much money though, what i have is going towards funding a commercial indy game atm. Fingers crossed I can make a profit.
I have been idly thinking of this exact idea for a while now but it needs money, pragmatism and meticulous planning, no fluff, bs or false promises, like so many other amiga projects.
I think it could be potentially more viable than say the armiga campaign at indiegogo, it looks like they won't be funded.
The armiga is not a very exciting proposition anyhow imo.