I think a free version of OpenBSD would be a good idea. I like some of
the aspects of the project, especially regarding security, although not
the aversion towards copyleft.

You might want to check out the Trisquel issue tracker for examples of
GNU FSDG issues that the project faces:

https://trisquel.info/en/project/issues?text=GFSD&projects=&status=All&priorities=All&categories=All

Some slightly more difficult FSDG issues that Trisquel faces include
rebranding programs such as Firefox and Thunderbird (see the Trademarks
section of the guidelines) and changing documentation to meet the
guidelines. Note that OpenBSD provides Firefox and Thunderbird packages:

http://mirror.aarnet.edu.au/pub/OpenBSD/5.6/packages/amd64/

Regarding escrow I think you'll need a more specific set of conditions
for the release of funds (e.g. the scope of the project), where the
money will go if the project fails, project timeline, etc. I think
contacting the FSF for escrow is a good idea.

I hope that helps and best of luck with your project.

Andrew

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