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I am doing it... My local convenience store also sells tooth cleaners shaped like tiny brushes which I use. It does help a bit but not entirely
Is there lint packed into the bottom of the port? It's not just dust on the contacts making a bad connection, it's dust shoved into the bottom physically preventing the plug from inserting fully. I out my faith in smart ports and use the metal Sim eject tool, alternating with air. Canned air is best, but I've done just fine with a hard cheek-loaded puff. Both my type-c phones (pixel 3a, pixel 7) have shiny port floors (the 0) so it's pretty obvious when I clean it properly
On topic: I'm in the same boat as you. My phone still works and has a decent battery life, so I don't see the point of upgrading. I don't game on my phone, well, nothing resource intensive anyway, and setting up a new one to my liking is a pain.
The other criterion for me is whether the phone still gets security updates. Once those stop, it's time to look around. That may mean a new phone, but for Pixels you also gave Graphene OS as a possibility.