The return of swag post is very welcome, however I see a couple of tiny things that we could perhaps improve.
In the early years of Security.SE, giving sec.SE t-shirts to speakers at conferences and competition winners really drove positive awareness and growth, and I know getting t-shirts from other sites kickstarted my forays out to bicycles.SE, lego.SE etc. I see from @Catija's comment that this swag run is only going to be SE/SO due to costs/logistics, and there is no current intention to offer swag for purchase.
But it should be possible for this to be federated out - the logos exist, and small run printers abound in many countries, so could the management of smaller-scale swag for non-trilogy sites be handled by moderators of those sites?
My other thought is for users who haven't hit 100k or 250k on one site, but have a total rep across multiple sites (yes, I count myself in this group: over 250k across the network, but no more than 60k on any one site). Will there be a "Masters of None" swag package?