Hey CLINDELL,
My wife works in the industry and has a plethora of knowledge around DTC, Wineclub management, and tasting room management. PM me and I'll get you in touch with her.
I know there's a few around that do POS as well as have compliance integrations, I think VineSpring and eWinery have those, they hook or have the ability to hook into ship compliant.
I agree though, there should be a wino group ;-)
--Cheers
Brian