Is ledger something anyone has installed on a private cloud? I'm interested in using this with the cli but would love to know if there is a way to make it a little less centralized but still secure?
Also, if you encrypt it using GPG with multiple keys, it will allow only a few people to work with it. Probably best to write a script that does it because not everybody understands how GPG works ;-)
Another option to consider is Fava. It's a web frontend for Beancount which is another plain-text accounting tool similar to ledger.
There's no authentication or security on the frontend, but you could probably put it behind basic auth+ssl to start with.
This is what I currently do, and it works pretty well. I just have a regular git repo in keybase-git and have my ledger(beancount) files plus whatever scripts I need to import statements from various banks/credit cards.
The central point is the content of your data. Also incomplete datasets should still work fine with both ledger and this analytics tool. So, not sure how it could be less centralized than this.
Ledger files are plaintext, works really great.