@dc42 so I moved the printer closer to the access point, it now reports -49dBm and I have no issues with uploading (also just upgraded to 3.4.5, but that happened after the uploading issue was resolved already in 3.4.3 by moving closer to the access point) . However it is in a more office-y area which is not great for noise (was previously in an isolated room).
It appears it has nothing to do with the firmware, however I still find it strange that the WiFi strength at -65dBm (admittedly, not the strongest) caused upload errors. I can down-grade and move it back to the other area as a test if you are still interested in having that tested.