Do you run your oilers at max? Looks pretty dry and clean vs oil munged. If your chain was so oily that it wicks and seeps everywhere some of that tacky retentive oil might end up in the bearing (?)
Burying the bar or cutting hardwood seems to "consume" oil and maybe that's leaving everything drier on your saws? WD40 will liquid a bearing temporarily but take out any lube that's in there. For field fix maybe try needle oiler with chain oil - drip it in through the clearance experiment
Can you throw a strip of chain oil off the tip after a cut via revving? (onto dry surface 2 - 3" away) Sort of oiing benchmark. Some saws historically were light on the oiling and required a pump swap. Odds are against this on all your saws at once.
To be clear oil seeping and a wicking is not during cut but when saw stored.
I run all Stihl use Stihl grease only on assembly and haven't touched (oil or grease) since.