[usrusr]

wholeheartedly agree with your general assessment gparticularly the part where you consider yourself more a supporter than a subscriber)

What might be keeping them from going deeper down the advertisement lane: at some point it becomes indistinguishable from selling user data. Sure, with Strava you don't need the adtech panopticon to reach some very specific audiences, but without opting into the panopticon they are cut off from all established online ad procurement processes.

And also there is d) stop being so damn expensive. This alone might make the ad path pointless, it could well be that Strava just happens to be more expensive per user than maximum ad monetization could ever be. If my personal bubble is in any way representative they are already taking in a lot of subscriptions. What we can't know at all is how Strava cost is structured: is it dominated by devs? operations? brand people? Of it's operations then their options are particularly limited and culling personalized leaderboards from free accounts could actually be more about saving expensive queries than about pushing subscriptions.