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Aw, shucks, Thomasin! It's my pleasure to offer my experience to this forum, I hope it's helpful now and then. Over the years, I've been very fortunate to have made my living working with a very wide variety of materials and methods in painting and art-related fields.
None less than Rubens himself rolled paintings for transport! The best (only?) way is to roll the painting with the painted side outward, preferably over a rigid core, such as a card-board tube with a minimum diameter of 3". (the larger, the better!)
This way, any fine cracks that result from the stress of being bent into a roll will close up when the piece is flattened. Rolled the other way, (paint-side inside) unrolling the canvas may actually pop bits of paint off, if it's quite thoroughly dry and has become at all brittle. Of course, the older the painting, the greater the risk, since ultimately, all oil paint films will become brittle as glass (that takes over 100 years in most cases).
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