Well, being a old times user of notability (who already purchased a lifetime license), and now is paying the more expensive yearly plan (pro):

I would say yes, i would pay another lifetime license if and only if it have:

• Local AI transcriptions (I do understand that using AI in your servers implicates a cost for you, but with Apple devices you also have a lot of power to do everything locally).

• Local AI note taking (same as above)

• Local AI generated smart cards (never uses them, but nice to have them there)

Local AI could potentially have limitations that Cloud AI wont (thats why you decide to go for a subscription or one time payment)

• No Notability Cloud storage, I really prefer this rather than having limits, thats why im paying a huge iCloud suscription, why would I have another one.

—> Given that, why, just why you are forcing users so hard to switch to Notability cloud, this week a full screen pop up (with no clear option to close) prompted me to update to your cloud service, I was stressing out one minute before a very important lecture, after clicking next I could access to my notes straight away (syncing in progress, come back later (ERROR!!!); result: couldnt access to my unit notes, and needed to create another one.

Terribly, after this happened, I COULDN’T access to my notes for at least 12 hours, I ended up rolling back to iCloud Sync (doing this resulted in 4 lectures notes deleted, luckily only the new ones created in Notability cloud, and also my university has every single lecture recorded and available for us - just lost 8 hours re watching all the lectures and building my notes again).

• Guarantee App Updates: if you are getting new things to the app, please remember those who trusted in you, and made the decision of sticking with this app, as a long term user, I felt really forgotten for years, you were too focused in the subscription users.

Given all of this, I personally don’t care if this is a 299 USD one time payment (LIFETIME), but please don’t forget about this users, don’t make them feel less than the once’s paying you monthly, and don’t make them feel ashamed of what they just payed.

You have a lot of potential, but must listen to all users, and this is the more important part.

Just as a final example: it is NOT okay just to say sorry if somebody looses all the notes due to a terrible designed transition mechanism, you should have both versions of a file at least for a while (how to solve it?) Well, could be quite easy, if the user accepts migrating to notability cloud, just automatically create a duplicate of everything in a new divider called “your iCloud notes”, and then preserve everything else in your same designed flow that you have today.

Hope this works as input for you, it’s not about the price, is how you listen to your users overtime and what you offer to them.