This is somewhat similar to the old best eBay memories thread.
My favorites would be some of my purchases when I got back into the game in 2011. Looking at my collection history, that lot of 311 cards from SM was only $20.50, and contained 104 ships. It included many of my favorites and staples, among them HMS Lord Algernon and El Acorazado. I actually have the exact date saved in my document:
2/13/11: Lot of Pirates CSG Spanish Main Wizkids 311 Cards: $20.50
Many others are awesome to remember. My first 2 packs of SM. The 97 ship lot for $26 in summer 2011. Getting nearly all of SCS for $150 in November 2014 (now a great deal considering the rise in prices), along with a lot of BC from the same seller for another $50. Then the crazy low price per ship deals of 2015:
3/31/15: F&S lot of 146 ships: $9.99
9/5/2015: Lot of 434 ships: $70
If I had to pick one, I’d go with that SM lot for nostalgia, favorite set, deal quality, and gameplay quality and quantity. (works out to about $.20/ship)
What is your favorite purchase of the game that you’ve made?