Door window... open, stuck in a complicated way.

[drowningbitbybit]

Check the condition of the vertical guide channel felts.....they should be felt lined rubber sections.
(These guide channels extend below the window opening as well)
If the felt has worn through.....often happens, the glass will not slide easily against straight rubber (without the felt)

Secondly, the glass lift channel should have a rubber sleeve that locks the window into the metal lift channel section.....without it, you'll lose the glass every time when it sticks.

Thirdly, if the cable/ coiled section inside the window actuator mechanism arm is rusty, it'll be hard to wind up....down is not usually an issue.
If this is a symptom, forget about lubing it.....just replace the mechanism.
All these parts are readily available

The winder mechanism seems fine when the glass isn't in there getting stuck and it pushes the glass up stiffly but with no issues, so I'm confident it's the just the sticking window.

Ah, yes, the felt of the guides looks a bit ropey on the front guide, so I'll get a new pair of those... plus some new doorcard clips as I've never managed to get the doorcard off yet without breaking a few!