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The idea of having to trade a bunch of <50 dollar trades initially feels kind of onerous to me, when so much of my desirable trades is made up of duals, zendikar fetches and legacy staples.

I'd suggest a limit on number of concurrent trades as an option alternative to dollar amount.

Ryan here. I live in the beaches area and usually play when I travel for work back to Phoenix with my old EDH crowd. I've visited a number of local game shops but none of them are particularly convenient for me--probably will wind up at Villainous Lair and/or SD Games and Comics (Which I really like, despite the drive). Game Empire occasionally.

I play predominately EDH but am working on a modern deck (monowhite Nykthos enchants), and a standard deck (selesnya something or other), just to have.

I have a pretty decent trade binder at this point, and a sale binder from a buddy who no longer plays, and two monstrous binders full of my EDH staples.