I spent the morning complaining at my business partner about how nobody seems to be solving the transaction classification issue. Every site (xero, ynab, pocketsmith etc) seem to think its ok to push all the grunt work off to their customers. I actually spent a couple of hours in the weekend hacking together a script to handle smarter bank transaction classification for me. This couldn't be more timely - will take look and have a play!
Edit to add: also interested in having a system that can project based on previous expenses to help with cash flow forecasting. It's insane that with 3 years of nicely classified data in xero we still have to more or less manually figure out what the next few months look like.