Joshua from the Product team at Bench here.
Sorry to hear about your experience with us, Meekro. We try to provide as hands-free an experience as possible, but know we have work to do.
We're sometimes stuck relying on bank statements due to the poor quality of data coming from bank feeds. This means we need to wait until month end to finalize books (and sometimes later if a credit card statement has a late statement date), leading to the timing challenge you described. We do this to ensure your books are completely accurate and ready for tax-time, with no fixes needed.
To address the above problem, we recently launched a new feature we're calling Pulse, to help manage day-to-day cash flow and spending. We're releasing improvements to it every week. https://bench.co/blog/operations/cash-flow-pulse/
The manual classification issue sounds like a failure on our part. We should not be repeatedly requesting input on the same transactions. If you shoot me an email (joshua@bench.co), I'd be happy to help. From the Product side, we're experimenting with using clustering models to better tackle the problem and remove some burden from our bookkeepers.
Lastly, on the tax front, we've got you covered! Our ambition is to do exactly what you're looking for - handle bookkeeping and taxes together on the back end, so you don't have to think about it. We'll have a formal announcement coming very soon. Please reach out to your bookkeeper if interested.