I at several occasions asked what would be required, or what you would like to see in a 'new' Oldschool expansion? The answers were as varied as could be, naturally some said a simple 'why?' or 'wouldn't that defeat the purpose?', in which I admit, it would, but wouldn't it also be something interesting.
Others would say things like 'Old School needs Stifle and Damnation' or 'more banding and rampage' or 'hexproof creatures, more efficent beaters at 1-2 CMC'.
The most exciting thing to ask about M:tG is what if? What if Legends wasn't playtested and released as it appeared in early 94, what if 'Vortex of Chaos' was released instead of 'Meanderings'? (which became Mirage/Visions). What if Force of Will remained red? What if Ice Age had the original Duals like intended? What if that M:tG rpg was released, and WotC didn't buyout TSR (or acquire Pokemon)?
It's fun to think, what if?
It's also fun, to think 'what makes Old school magic magical? Can it be replicated? We all will disagree when the Magic ran out, but we will all agree that something truly amazing existed within the the first two years of the game, something that might not be replicate-able.
I thought for several months about this, and I think I have some answers. First the cards need to be have symmetical effects. Think the original crusade, while a few assymetrical effects exist in these sets, the majority of them effected all players, as was intended as a 'drawback' at the time. Second, simple, easy to recognize tropes. Magic is littered with classical easy to recognize tropes, from the goblin king straight out of The Hobbit, to Cosmic Horrors, Muscular Barbarians, battle ready angels, vampires, and so forth. Finally, real world flavor text, which I always felt was a great shame they did away with.
Also these mechanical set ups:
First: Long winded, strange cards, but flavorful cards. Things like Remove Enchantments, Tangle Kelp, Goblin Kites. These cards are long winded, but excel in flavor despite their rule heavy text.
I feel this enchantment here shows what I mean. The concept is clear, two allies fall in love in combat, which allows them to fight more effectively, and with each other. However, when one dies (or god forbid the enchantment is destroyed), it's lost forever. Actually this one is probably a bit to rule heavy to truly be an 'old school card', but it certainly feels like it could be.
'Can't be destroyed'
Believe it or not, two cards that are in 93/94 have to deal directly with indestructibility. These cards are simply Concentrate Ground, and Guardian Beast. However, it shows the idea was there, from the beginning. I figure'd another card that had a similar cause would work well.