The biggest problem with Winter's fury is the graphic. That may not matter to some but just beware that it has the rusty/finesteel longsword graphic.
I used a Trak tooth all the way to epic but I was poor as the rogue was my first character. There is also another 10/20 dagger from Chardok that I have seen for about 500p or so, the Sarnak Backstabber. Like a Trak tooth with a few stats.
I personally think your option #2 would be better if it's between those 2 setups.
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[60 Assassin] Cloke (Halfling)
[60 Warder] Keyx (Wood Elf)
[56 Luminary] Budzo (Iksar)
[51 Champion] Logue (Halfling)
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