Cookies required for the website to work (like that one) are totally fine and, in fact, they don’t even have to ask you about them - if they’re not used for tracking. So no, asking each time is definitely avoidable.

Late reply, but for me personally, I started doing it because my Keepass database is already accessed using two factors (password and key file). Therefore, I’d gain very little by keeping the second factor of those sites external - essentially, those second factors are compounded into the second factor for the database.

Sorry, I mistakenly assumed you were talking about disk storage - sure, if you’re designing your own solution, definitely use tags! Although the ones Gmail uses aren’t really portable in my experience, so you’re forced to use their mail client. That, however, is pretty much unavoidable if you’re putting a new spin on established protocols like they’re doing - maybe those changes will get picked up by other clients, maybe they won’t, who knows?

That’s true, but since we’re stuck with the file/folder system for all intents and purposes, you should be able to replicate that behaviour by making those tags part of the filenames (like rent_lease_landlordX.pdf) and searching for (parts of) filenames instead. But yes, a dedicated system would of course be preferable.

Why not just use soft links instead?