Have you ever thought about using a natural language interface with ledger? For example, the Mac/iOS calendar app Fantastical lets you create an event by typing or dictating a sentence like "lunch with mike at 2 on Tuesday at Wendy's", and the app will parse the input to create an event with the right parameters.
I ask after reading your vacation write-up. Seems like the input side could have been a lot easier if you had a speech or text NLP interface to ledger. "$10 entertainment expense paid from MasterCard today," for example. That could be the holy grail for people who are not inclined to keep a detailed ledger, or for situations where input is difficult. (Theoretically you could email/iMessage/SMS/slack that string and have it picked up by your ledger file.)
I ask after reading your vacation write-up. Seems like the input side could have been a lot easier if you had a speech or text NLP interface to ledger. "$10 entertainment expense paid from MasterCard today," for example. That could be the holy grail for people who are not inclined to keep a detailed ledger, or for situations where input is difficult. (Theoretically you could email/iMessage/SMS/slack that string and have it picked up by your ledger file.)