Well, from a technical standpoint, manually pulling a list of GMs who have earned a new star should be an easy database query. That shouldn't be more than an hour's work for the IT folks to write the query. Then it would only take 2 minutes to re-run the same report to give Mike that list every few months. Maybe this could be done quarterly or something, rather than as soon as someone earns the star.
Just writing a database query to pull a list of GMs and their stars would probably only take a few minutes... but doing thing the "right" way would take a lot more effort that that. Paizo would also want a way to track which boons are eligible prizes for GM stars and track which GMs have claimed prizes for their stars, both of which are probably new database tables. They'll also want a GUI that campaign coordinators can use to manage which boons are available, plus an interface for users to see which ones they're eligible for and then claim them, and it would also need to provide a mechanism for users to download them. You've also got to factor in time to test all of the new GUIs and database queries, since you don't want to put them on the production systems until you're sure they work right, and you also have to consider the cost of taking the production system offline while you upgrade it.
Without any knowledge of Paizo's internal structure, I'd probably estimate that as three or four days of work for one developer. It could definitely be more, depending on how flexible their system is. That's not a whole lot, but the budget for that still has to come from somewhere. (in the real world I do software development, mostly web & database stuff nowadays, coincidentally)
Anyway, as a venture officer, I wouldn't mind tracking this kind of thing manually. I think a reasonable interim solution might be to provide access to the star boons to VOs and have GMs who've earned stars go to their local VO to request a copy of a boon. To be fair, in my local area, even if every GM came to me right away and wanted all the boons they could claim, I might only have to give out a few dozen; I'm sure there are other VOs who would have to deal with a lot more paperwork.
On an unrelated note, I've really been thinking about making a kitsune mysterious stranger gunslinger. I've already got a kitsune sorcerer, though, so I might go with a half-elf musket master instead...