[hijack]
Ki Ryn said:
That's really funny (in a scary kind of way) that you EXPECT the DM to put tailored magic items in your path. For me, that ranks right up there with the DM fudging rolls so the PCs always win. I know it happens in some games, but not in any that I would ever be a part of.
I guess the first question is do you want your players to be interested in the loot they find?
There gets to be a point where the PCs have so much cash, that unless the NPC spend almost all of their gp value on a single item, the party won't care and simply sell it anyway. But if he makes an NPC that uses the same weapon as your PC, and it has "cool" powers that yours doesn't have, would you be interested in it? Maybe not as a replacement but as a secondary or a back up weapon? (Such as if yours is a flaming sword and the NPC had a ice style sword.)
How is that different than saying "Player 1 hasn't had a session built around him in a while and I think he'd like a new weapon"?
I am in no way saying that every session should have an upgraded weapon or even that every session built around Player 1 should have his kind of weapon. That would lessen the 'cool' aspect of finding your new toy and go a long way to make finding a new weapon to accually be boring. Giving them their weapon of choice can easily be a reward (a story bonus if you will) for going through and advancing their indavidual plotline.
Putting new weapons/armors/toys into the game specifically for the players does two things: first it says that you, as the DM, like the character and want the character to stay; second it makes the character history more interesting by being able to say "I got this sword from the Red Dragon hoard" or that you "pulled this bow off the body of Kilaren the Thrice-Dead" or they "received this shield that has my family crest when I saved my sister from my murderous uncle".
[pulling jack back into the topic at hand kicking and screaming]
That said...
If all you do is random treasure the retraining may help keep the players interested in the loot. If no one has spent feats on using an axe there may now be a reason for them to be interested in the axe you rolled up.
Or taking it a step further, if you roll up an incredable double-bladed sword (or some other exotic weapon) that is better than anything the group already has, now there is a way for the players to actually want to keep it.
If a player has been using feats on the sword since the beginning there is no reason for him to drop the sword and pick up the axe. Maybe for special material puposes but he won't stop using the sword as his primary weapon and the axe will just be the silver weapon or the adamantine weapon - not the Chilled Dragon's Axe Deadly Iron. If, however, he could start training with the axe and become as good with the axe as he was with the sword without spending eight new level's worth of feats (just, say, four levels to replace them all but no new feat slots are spent) he might just be excited enough about the randomly rolled axe as he would be about a new sword. Otherwise the specacular roll for the powerful new axe will just be sold for gp and the weapon you yourself are excited about will never be used.
If anything, I think the retraining helps the "100% random loot" style more than it helps the "order a toy" style of play.