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There is a My Little Pony subscription box already, the My Little Pony Express, that's mainly for G1. I think if you bring something different to the table you could get some interest
My only concern would be the ability to keep up with orders! Making more than one custom pony per month PLUS various custom items sounds kind of impossible! And easy to get overwhelmed!
How about, instead of a subscription box, you'd offer mystery boxes? It would be pretty much the same thing but without having to worry about doing it regularly in case it gets overwhelming, since you could offer them as often and as many as you can produce. You could even vary the contents - say, offer a variety of cheaper boxes with only a couple of items and more expensive ones along the lines of your description above. If the boxes (whatever the format) contain non-custom ponies and official merch in addition to handmade items, you may post them in Sales. Just a tip to ensure you'll get more views!