The writing is on the wall. For more than a decade, DayOne has been my go-to journaling app. It’s comfortable, natural, and intuitive. But alas, I feel that I must transition to Apple. If for no other reason, Apple’s Journal app has a better chance of enduring long after I am gone, and a journal must endure.
I also had hoped that DayOne would develop support for Apple Pencil. They had a decade to do it, but they never did it. Journaling and handwriting are like burgers and fries. Huge missed opportunity! There’s something about natural handwriting that’s therapeutic, you know? It’s an extension of the author’s soul.
Now, how do I transfer all my DayOne entries with embedded photos and videos onto Journal??
Day One will still likely be around for quite a while, I predict. It's already been around for 14 years. As a product, it really isn't growing or evolving much and largely seems to be in "maintenance mode" (I've been rebuffed twice by their support staff, for some valid suggestions on UI readability and usability), but it has been a stable journaling app and paid service, at least for me.
Apple is just getting started with Journal, so the product is not as refined or capable as Day One.
Ultimately, you're at the mercy of the provider when it comes to entrusting your data via these cloud-based journaling services. Keeping a journal that's going to last well after you're gone is probably not something you can expect from a digital service. Even if your children or loved ones want to read what you left behind, there's no guarantee that they will be able to access the data, or that the service will still be there. Paper and pencil/pen probably still last a lot longer than these digital services, even though theoretically your data should be able to be copied and recopied and transferred between services and providers ad infinitum.
Being dependent on safekeeping your memories in any digital format assumes that (1) it will remain readable and accessible for years and decades (centuries?) to come, and (2) it can be stored reliably. Both of those are pretty tall orders for digital data. Better to expect that your data will not survive your passing. Personally, I don't expect that my kids or significant other will ever have any interest in my journals after I kick the bucket, whatever format I keep them in. I mostly keep them for myself and my own record-keeping and mental well-being, if you could call it that.
As for handwriting, handwriting input with Apple Pencil is already supported on iOS/iPadOS devices. It leaves a lot to be desired in terms of accuracy, though. Maybe you are referring to actually using handwriting and not converting it to text data. In other words, creating image data.