And yes, "cash cow" seems a little uncouth in light of that discussion, haha.
I see the attraction of a sub as implicit copy protection. So I wonder why there aren't more ISVs putting the yearly sub markedly lower than the former licence price.
Scrollaway makes great points about microsubscriptions. I think he's right that a central place to easily manage multiple subs would take away most of the pain. Banks seem to specialise in awkward UX and statements that just show "UnknownCo LLC Service" because they're the parent company of coolthing.com's service. Patreon might be better placed to have a try here.
Right now I'm having this battle with myself as the side-project I'm slowly progressing looks like having a sub might be right. I'm still reluctant. Oh the irony. :)
Good luck with your creations.
If a service is worthless without the online component, Netflix for instance, a sub is clearly the answer and I'll pay gladly. For an editor, utility or IDE having an online account is usually, for me at least, a minor benefit at best when I'll put my files in iCloud, dropbox or git. You made it a tougher sell as you want a rolling commitment. £50 as a one off? I'll spend that on a whim, then probably upgrade in a couple of years.
Most examples I've seen of companies switching to a subscription model end up with a subscription that's more than the previous licence cost. Unless it's something your career or business depends on few would buy every major release widening the real differential further.
That we're having this conversation on a post about a "cash cow sales model" says it all don't you think? It simply starts to look like "we'd like more money from you".