Thing 1:
Not a lawyer, but my reading of his license is that as long as you are not reselling or using commercially, there is no problem. A group buy of any sort (including having boards populated) for hobbyists should be fine by the letter of the license. If there is concern that it violates the spirit, that could easily be cleared up by communicating directly with him.
Thing 2:
I think
@Tomc938 mentioned in some earlier post that I can't find that there are a couple of different paths being discussed here. I think these are (please clarify if I'm even more confused than usual...it
IS a Monday morning)
1) Tom has a few bare boards available, there could be a group buy for components for these to be individually populated by whoever buys them from him,
2) @
slow-poke is reworking the design and a group buy for components for this could be done with sufficient interest. I assume (?) this design implies a new board spin - it would be different enough that Tom's boards would not be usable even with a number of, for example, (ahem, well documented) jumpers and trace cuts,
3) Enough interest to justify Slow-poke's new board design not just being produced bare, but populated by a suitable service company, and ready to go boards delivered to the participants.
Just for the record, I'm on-board for whichever of these paths develops.
I will say that with the two small companies that I worked for that designed electronics*, the first spin of a board ALWAYS needed tweaks. Going direct to populating the boards from a brand new design does carry an element of risk, even if it's a small as "Oops! Well, a single jumper or additional pull up will fix that".
*Not my role or skill set, I just wrote software and in one case pretended to manage.