I automated downloading and reconciling my financials from all my bank accounts. https://disjoint.ca/projects/ledger-reconciler
I've been working on my own classifier for updating my ledger because I struggled too much trying to get other people's stuff to work. I'm getting about ~90% accuracy using a SVM from scikit-learn, but it can only ever be semi-automated. My plan is that every month I'll go through my various accounts and help to update my ledger. One thing that I don't think other software does is automatically remove the duplication…
This in itself has saved me so much time that I can deal with manually editing the occassional duplicate entry (internal account transfers). I also keep all my ledger data in git so it's very easy to see what has changed, etc.
Have you looked at the reckon gem[0] for auto-classification? That is basically what this program uses.