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Transfer from gen 1->2 required a second gameboy and a link cable. That's about 40 bucks for a gameboy and maybe about 10 for a link cable.
2->3 Non existant
Gen 3 Storage (Pokemon Box GC) was it's own game, so probably about 20 bucks
3->4 The ONLY free transfer method
Gen 4 Storage (My Pokemon Ranch) was an eShop game, so it was probably about 10 bucks
4->5 Requires a second DS. Assuming you go as cheap as possible you could get a clamshell (the fat DS) used now for about maybe 50 bucks.
All this in mind the fact that you're paying 5 dollars a year for both transfer and storage means that you're lucky you're paying so little.
