My major gripe with hledger and other plaintext accounting systems: setting up the correct rules (regex for your expenses) takes too much time as it involves:
a) defining the regexes/categories) for dozens to hundreds of expense descriptions (e.g. walmart, gas station xyz)
b) "recompiling" your hledger journals after every rule change
c) checking for negative and positive errors (expense description was not matched OR too many different expenses were matched)
This process is much faster in a spreadsheet application. IMHO the journal format of hledger and other plaintext accounts apps is too verbose.
it would be a great relief if someone started a Github repository with expense texts used when you e.g. pay at Carrefour in Italy or Walmart in the USA with your debit card. People could submit those descriptions from the CSV exports of their bank accounts.
Another annoyance in Europe is that there is no API connection for open source apps to bank account statements, you always rely on manual CSV exports.