A little late here - but I adore YNAB. I'll talk about it all day but at it's base it functions off of a digitized envelope system rather than trying to match projected inputs to projected outputs every month.

YNAB has the automatic uploads of transactions (and does try to guess a category for you but you do have to review and approve).

It is fairly expensive. Although the family plan works if you have anyone you're open about finances with (or simply trust the family "owner" not to peek - like my younger sister decided to trust me not to look.)

How is he doing?

I wouldn't mind calling some vets and asking for cost estimates to help out from a distance.