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The only issue I have had with my P250 40 cal in a Supertuck has been with the Velcro clips coming loose from the belt and working its way up on my pants, Although I haven't worn my gun while on a horse unless your using Velcro clips you shouldn't have an issue. I have been on play ground equipment with the kids and have never had a retention issue. you body will hold the gun in tight. Don't base retention on the gun in the holster with out it being on your body. If your planning on Velcro clips buy some from Comp-Tac.
If your going to be in a hot environment and not where a undershirt get the horse hide, it wont absorb sweat and wont stick to your skin.
I have both the Super Tuck and the Comp-Tac Mtac, they are both great each with their pros and cons.