Love your self-awareness here. I have a couple thoughts.

First let me say that our magic journey has several mirror points, from the move into legacy in 2012, then modern, then old school and the changing of circumstances around friends to play with along the way. (I now mostly play old school over skype and a couple times a year in person when I meet up with the old school community for events.)

The things you say always really resonate with me.

Thought #1. Every truly great spec I’ve made comes from *playing* magic. I first learned about Shadow of Doubt by getting blown out by it at a modern PTQ. Bought many copies, it spiked, I sold out. Same with Kolaghan’s command. I was a competitive Affinity player and someone killed me so hard with a K-Command I could actually feel it sting. I immediately went and bought a large number of foils and non-foils. Arclight Phoenix is on the same list. Playing is the basis for in-context card evaluation. IMO you cannot properly position yourself in MTG finance if you don’t play the formats you invest in. I bought a CE Lotus for $300 right before it spiked because I was playing old school and found out EC rules allow for IE/CE. We learn the value of the cards from their function and legality in the context of play.

Thought #2 is a takeaway that I have from this article about Alpha 40. You’ve played and realized the design space is extremely limited. The format started as a joke. Format creator Magnus de Laval has literally said it’s a joke (link :http://geocitiesofbrass.com/alpha-40/)

“It could be notable that this “format” was mostly made as a joke to avoid making an argument in an online discussion, and an excuse to meet international players in a pub the day before n00bcon ?

Anyways, people got excited and in the weeks following the announcement many of the common/uncommon Alpha cards saw an almost ten-fold increase in price. In the end we were almost 60 players at the first Wizards’ Tournament, the first gathering of it’s kind since September 1993. The idea took off from there, and for this years Wizards’ Tournament 100 players are signed up. Not too bad for a joke”

So yeah, the prices skyrocketed from people just wanting to play around with ancient magic cards in Sweden, but are these cards you really care about owning to play magic with? If not, I’d sell them. Old school players will move on to the next thing. See #revised40, a much cheaper and wider format.

If you are genuinely buying cards you want to play with because they are good or fun then you can be much more certain you’re making a good finance purchase. After all, you didn’t hang on to your copies of grave robbers because it’s a good card, but because you liked the art. A card being not playable is the easiest way for the price to contract. That why I worried when you suggested buying “any beta rare” in a recent article. Don’t do that. Buy a good beta rare that’s fun or powerful, even if it costs a little more. This is how to make old school finance like blue chip stock purchases. You may not hit the spike, but it’s less likely to retract.

If you ever want to skype battle some old school I’m down. @benjaMTG on twitter.