Sorry but no. You are not meant to keep and only use the same weapons or armor from year 1 all the way to the end of the game. Get over it and move on.
No they do not have to respect any amount of time you put in the game at all. Get over it.
In almost every other mmo based game you have to change gear as you upgrade and get better. you dont get to keep lower/older gear and have it do as well as newer/higher gear.
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more than likely will not happen and each year will be the same dilemma for people. and this is how ti is with any mmo based game. for there would be no reason to buy the dlc and play it if not going to try and get the new armor and gear from it.