I’d gladly pay $1000 over a decade for a crucial tool. If the concern is open source and true longevity, I get it, you don’t get that here. But cost for value? Holy shit. $1000 over a decade is absolutely worth it for something you depend on.
If you’re a regular at a bar or restaurant, you pay an order of magnitude over $1000 a year for THAT service. This one is probably worth more.
I can, however, relate to the “every five years my system changes” problem. It’s not fun. At the same time, this is a reasonable cadence to re-evaluate things. If you found something perfect for you that works >5 years, holy crap. You are blessed. That honestly should not be the standard for tools these days—ESPECIALLY in a today’s world.
All that said: I don’t knock the author for trying to build software that can work for someone for 20 years or more. I salute that attempt—and I hope they can do it!—even if I think the specific details of how they got there are flawed.