I realize that the Stack Exchange store closed due to logistics. Why not re-open? I understand that 'swag' feels better when you've earned it, but can't you at least make different shirts that say something like 'Trusted User' that differentiate the swag earned and the swag paid for?
Also, who says that you have to handle the swag sales yourselves? I know that recently, a Stack Exchange shirt appeared in Startup Threads bags- why can't you ask Startup Threads to handle the sale of your shirts for you? For dealing with slow sales, why don't you have set limited-time timeframes where users can purchase it, just to make it a little bit more exclusive and produce a sales 'rush'? (kind of like MailChimp, except their shirts are free)
All questions summed up: In light of all these solutions, is it possible for the Stack Exchange store to open again?
update: I recently got a hold of Frank Denbow from Startup Threads, who said that he might look into setting this up for SE- all we can do now is hope...