Yes! Budgeter here as well :) My YNAB subscription is well worth it, BUT I use YNAB at least weekly. That was a big struggle I had with coming up with a pricing model that made sense here--realistically, it seems like most/many people will only be actively using Itinee for relatively brief periods of time throughout the year, which, at least if I were the customer, would make me wary of long subscriptions.
As a developer/founder I absolutely would prefer regular subscriptions to sporadic one-offs, I just doubt(ed) if people would actually signup for that.
I certainly agree that transitioning to a subscription model would require lower prices to be feasible and may be sufficient to get people on board with "wasting" their subscription for 75% of the year.
As a tangent, I find that it's really hard to get this kind of feedback from real/potential customers (like yourself!) but such feedback is incredibly valuable (thank you!). I wonder if there's a market for some service where I could pay $100 for 3 people to go to my landing page, try my product (free of cost to them, obviously) and then be open to some conversation about their experience. It seems like there could be a market for that given the "Indie Hacker" boom. Maybe such a thing already exists.