It's odd, in the past couple of months I haven't had Gale ask me once for a magic item. Not sure if this is related but I also haven't been able to romance him. During the party after killing the goblins he'll mention "you gave me magic items when I needed it", even though I didn't and then want to talk the night after. I had "Exceptional" relationship with him, so it's not like he thought I was a jerk. At any rate, at no point did he ever ask for a magic item, even though I had the sword of Tyr, the iron flask and the amulet of Selune. I gave the Necromancy of Thay to him, but that was to read and it's still in my inventory.
Is his need for magic items tied to the tadpole? I tend to use the tadpole a lot, so maybe his need is suppressed? Does he need to die once (and go through the true resurrection scroll bit)?
I don't think he needs to be resurrected first. On my very first run (before patch 3 though) he died for the first time in the Underdark and he had already been asking for items. In all other runs, I just let him kick the bucket the first time he was knocked out (which means pretty soon), so I'm not sure if something changed with patch 3. But he does seem to bug very easily if you don't keep him in the party (and maybe even if you do). I usually try keeping him in the party until he tells me he needs magic items, at that point I feel confident I can kick him out without messing up his conversations. I also read somewhere that if his approval rating rises too fast in between rests (which can easily happen if you're doing a good run) you may miss the conversation about his condition.
I don't think you can romance him if he never tells you about his condition, but I am no expert. I only romanced him once and I haven't even gotten as far as the party yet, but I did get the "weave" scene which I believe is what opens up his romance option at the party.
