Mr. Mason-
Having destroyed a tranny by towing it a long distance I can give you a description of the symptoms that resulted.
ALL the syncros were COMPLETELY shot. (It had a four speed syncro tranny that was a lot of work to install in a 67 MGBGT.)
You had to FIRMLY hold it in every gear or it would pop out.
When I drained the oil a lot of rather large pieces of metal came out.
You could still drive the car but you had to very accurately double clutch on up and downshifts.
I would say that your idea about the oil not getting where it needed to is accurate.
If you think about it, when a car is typically in neutral , the input shaft is spinning and the output shaft is not.
When towing , the opposite occurs. Not good.
Also, on a long trip I wonder if the shift lever bounces around a lot and the gears try to engage.
Additionally, all the oil is tilted to the back of the tranny due to the nose up aspect of the car. This cannot help the situation.
Anyway, I can tell you it was a hard lesson to learn .
LCJUTILA