I had around 80-90 ponies in my original herd.
Bowtie was first. (birthday gift from grandparents)
Baby Moondancer was my first baby pony. (birthday gift from babysitter a year or two later)
Sweet Pocket was my last pony. (my mom bought it for me at the grocery store while I was sick)
I actually don't remember the first pony I bought when I started collecting again! I remember I was in denial that MLP weren't sold in stores anymore. It was a couple years after G2 died and before G3 came along. I think I just bought randomly the ponies I liked on eBay, I definitely went on a binge. One of the first was a custom but I don't think she was THE first. I remember I wasn't totally clear on what a custom was and didn't realize I was getting a hand painted pony.