Reading some documentation about using hledger, a particular passage jumped out at me:
It should be easy to work towards eventual consistency. …I should be able to do them bit by little bit, leaving things half-done, and picking them up later with little (mental) effort. Eventually my records would be perfect and consistent.
This has been an approach I've used for many things in my life for a long time. It has something in common with eat the elephant one mouthful at a time. I think there are some categories of problems that you can't solve this way: perhaps because with this approach you are always stuck in a local minima/maxima. On the other hand I often feel that there's no way I can address some problems at all without doing so in the smallest of steps.
Personal finance is definitely one of those.