Ex dragon charizard 100%. Such a beautiful Arita piece and such a realistic feel to charizard.
Gold star charizard, better art than base imo. On the japanese side, you could land a quite clean raw one for $2k, or a PSA 8 with some change leftover
Spanish Base Set 1st Edition Charizard PSA9
Stormfront in PSA 9! Iconic card
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Blaine’s Charizard for me!
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I’d probably get the e-card promo Zard, a psa 8 shadowless for my set or the ex zard from frlg.
PSA 9 and lower holo wotc cards are pretty underrated imo! Great value for NM old cards!
CGC 9 1st ed. Blaine’s Charizard no question. That should fit neatly within that price range as well.
As for underrated WOTC cards…that’s a tough one. There’s potentially so many answers to that question. One that comes to my mind Giovanni’s Nidoking (one of my faves). It’s card art and moveset at the time were actually realyl good.
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Base Set Shadowless - nothing beats classic!
You wouldn’t get this for 2k, Christ lucky to get an English one for that
Selling the 8.5?
Probably plasma storm zard and flash fire
Investment wise, shadowless charizard, gold star or if you get your hand on a beat up version of for position only charizard.
1998 CD Promo PSA 10 is 
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Shadowless in a heartbeat
This depends on motive. Are you spending 2K on a Charizard because you love Charizard or because you’re “investing” in Charizard?
I agree for 2k, I’ll buy a charizard trying reaching the moon. As they say “Black is the new Orange” 
… then if you stick a Label on it… I may not though 