I asked about monogramming in my boutique. The person that does most of the monogramming happened to be in earshot,so she came over to explain what's going on. They're waiting for new machines - bigger ones, so they can do bigger pieces. The one they have now is primarily for hang tags or small leather goods. New colors are coming as well (and they suggest giving you the option to use different contrasting colors, ie, not the same as the lining color - make it unique).
As to how it will wear - she said they put a sealant over it in the process - so it shouldn't fade or crack for years. Provided they did it correctly.
Are you east coast? She said west coast has been slow in getting the new machines - so I may have to wait a couple months to get mine monogrammed[emoji30] They're hoping well before the holidays so they can offer this option on any bag - not just the Saddle Bag.