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Should go into a gallon freezer bag?

My point as in 'so inclined'!
A new Tony Miller strop would not be as inclined to crack the surface as rolled to the inside as an old-untreated strop would be.
Hence the difference!

Good point! I always roll them loosely with fabric out. No crack the surface of the leather if it is so inclined.

Loosely, now! ;)

Yeah, there is a med priority box for the same dough which is taller, yet not as wide/long. Costs the same.
That is best to loosely roll it, I think.

Flat makes for pricier shipping. Nothing wrong with loosely rolling it and putting it into a box, IMO.