I made the switch to hledger about two years ago and I have struggled using the command line to input my transactions. Right now I use my text editor (nvim) and a snippet engine for my common / recurring transactions. This may be a little more work than just setting everything up to work automatically, but I like it. For reporting, there are some tools which can help with that, I used to use hreports [0], but have since switched to my own script, which exports the data from hledger and queries it itself.
A good (although opinionated) resource for learning how to use hledger is the manual, which goes in depth about different accounting and modeling concepts [1].
A good (although opinionated) resource for learning how to use hledger is the manual, which goes in depth about different accounting and modeling concepts [1].
[0]: https://hreports.readthedocs.io/en/latest/readme.html
[1]: https://hledger.org/dev/hledger.html