I just picked the last of the medallions (the 15th), before entering the church. The merchant doesn't have an option to updgrade the Punisher (I got it right after I shot the 10th medallion), and it doesn't happen automatically...
You get more upgrades the further you progress in the game; you won't be maxing out any gun any time soon.
And you really shouldn't upgrade your guns until you get a Red9 (or Blacktail), TMP, Semiauto Rifle and a Striker. Upgrades aren't prohibitively expensive to start off, but the bonuses for upgrading are extremely small for inferior guns and you will need the money later.
Don't upgrade the Punisher ever.. Its a crap pistol compared to the guns you will get in a few.. The Red9 and the Blackfin ( I think thats the name) are superior pistols.. And the Red9 you will get very very soon.
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