That said, I think we should be careful with our assumptions about how much influence we can buy with the money we have.
Sure. Let's not make assumptions at all then: what makes someone think that calendar is amenable to WMF-mandated development? Already one year ago, I proposed that Phacility be hired to upstream our issues (and triage them upstream). https://lists.wikimedia.org/pipermail/teampractices/2015-March/000642.html
The reason is that so far I'm not aware of a single person in Wikimedia being able to talk with upstream (as opposed to talking past each other). https://phabricator.wikimedia.org/project/board/6/query/all/ seems to prove none exists, as the "Solved upstream" column lists a whopping 2 issues out of 500+ upstream issues.
Phacility could file the reports upstream in the way they prefer and optionally put a price tag on each request, without continuing to waste our reporters' time.
Nemo