I feel the "Pay once and get x years of updates" is a good balance I'm super tired of subscriptions but I understand that SOME apps need to have that model

Interesting thought! How many years would be reasonable in your opinion? Like 2 years or so? I have one app that does that annually, but calls it a "pay once for 12 months of upgrades" instead of an "annual plan"... which is basically what it is 😂

Most software just keeps iterating until it becomes a Frankenstein

True; disciplined product-led teams can fight that though

I'd hope so, but unfortunately the market tells a different story. Product teams can only make compromises, they can't fight external pressure from the stock market or venture capital.

I don't think I see an appreciable difference (in terms of iterating/improving) between the best of each that I use, but I def evaluate subs at renewal to see if I got value from them in the past year.