I suppose it depends how and how much you use it. I would rather pay $100 for software I know I'll use for years than pay $5/month in perpetuity, especially if I can support a smaller software developer.

My justification was that in the city I was paying something like $150/year for an unlimited pass and saving by cancelling a $120/month unlimited Metrocard. And as I mentioned, it was by far the best bike directions available at the time. Shortly after, Apple released bike navigation on Apple Maps, but I still preferred Bikemap for its routing. I'm still annoyed from missing out on AllTrails when they offered a lifetime license...

It appears Bikemap doesn't always have the lifetime license available anymore, but they offered it last summer. Maybe they'll bring it back again? (Apologies for the Facebook link.)