Hi Deb - I am laughing at pretty much every sentence you wrote because its like I wrote them! Especially the parts about not having fancy nails, going out to eat at nice places vs taking a great lesson, and the "older I get the more into horses I become" - I am right there with you. As my teenagers get closer to college age the horse obsession is becoming unstoppable!
At one time I had very very pretty nails; always perfect, had gels, kept them short so that it didn't impair my playing much but felt unprofessional without them. I too would rather spend on things that matter and I make sure to tell all the palm beachy fancy people I play and sing for that I am a horse girl so that they put two and two together and realize that I can't have the foo foo nails and function as an equestrian (physically or financially!) I still have foo foo outfits and hair though. You have to appeal to them on some level they can relate to or they get uncomfortable - especially the ones that are mostly "man made."
You also mentioned the crazy idiosyncratic ponies that taught us when we were little...I think about those times a lot...not to put down formal instruction or anything but I honestly think that the way our parents did it (set us free on a pony with only a bridle, lead rope "reins" and no saddle for 8 hours, 7 days a week of summer) was a better education than any riding academy could have offered. But that was then and nowadays we would have to live on top of a mountain in Montana in order to feel like everything would turn out ok.