Basically, it will probably be like what happened in TTK. We didn't really have to "start fresh", but with the expansion there were green drops more powerful than the current legendaries we had equipped. So I imagine it will be something like that. Our guardians won't be reset, but our stuff just won't be powerful enough to use in Destiny 2. I'm sure they'll drag it along like TTK too by reintroducing exotics in increments and expansions.
There will likely be some changes to subclasses as well. I can see us being sapped of our light or something as an excuse to reset that kind of progress, but we find and activate new more powerful subclasses as a result or something. Anyways it's all speculation, i mean, at one point I don't want to lose any progress and I'd like to use everything I've earned over the last couple of years... But at the same time, in a new game, a sequel, it's kind of hard to justify not starting from a fresh point.
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I would like to see weapons and armor go forward but allow us to earn the ability to power them up if we chose. For sub-classes make it into a true Talent Tree where we can pick a certain number of options. But balance it in such a way that it isn't uber powerful. The artifact system we are getting in ROI is kind of what I mean as you can choose to give up some things but get others. I just like the idea of really making my Hunter different from others and not saying well today I will play as this subclass.