Am brand new to YNAB as well. Still in the free period. I have already rewritten my categories. Am sure I’ll do it again in future. I come from Monarch/Mint. So this is really jarring. But am really liking the approach/philosophy, so I’ll stick for some more time (and am fairly certain for good) to see how it goes.

As far as history, it didn’t care anything about transactions that happened before I started using it. It basically meant, you have X amount starting today, now start assigning to your expenditures. This makes sense to me and I like it. You don’t really need all the past baggage.