Intriguing stopgap proposal. As the site/users grows, would still run into math problem of running out of Strava API calls eventually. So this would be a little bit like kicking the can down the road and worrying about it later.
I do like that it could lead to more supporters and thus more money for James which may open new avenues/opportunities (ex: more servers if needed, part time developer, etc). However, it would create an unfair elitist vibe to the site (e.g. only those that can afford it, get it). This may be what you mean by “going against CityStrides philosophy” in another topic. We do live in a capitalist society though so it’s not like this would be out of norm.
Re: “James isn’t in here…” @JamesChevalier is everywhere 