The reasons why I tried and failed with ledger:

- I never quite understood how to 'start' the ledger balance. Should I start on the first of the year when my account was at $56 or today when it's at $76 ... where does this $ come from?

but probably more this:

- I found it super laborious to enter transactions. I guess I grew up post-checkbook but when I'm not near my computer for a few days and have a pocketful (or not) of transactions to enter, I would get behind and then just give up. Even with logging into my bank account to cheat.

- Investments man. How does one track dividends, buy/selling in a text file. I probably need to take a finance class... :)

I had the exact same gripes with ledger. Although there are means to pull csv-data from most banks, one still would have to categorize the entries on each import into ledger.

There is https://github.com/cantino/reckon which claims to solve this by automatically sorting entries into the correct accounts by means of Bayesian learning. \nSadly the machine learning worked unreliably with my data - I would still have to manually sort many of the recurring and previously "tagged" entries into the proper account each time they came up in the csv-file.