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Although it's a good idea to force the system to "rethink" our top witnesses by resetting the witness votes, I don't know how this will actually affect the blockchain. So, it's hard for me to just say Yes or No to your question.
We have to remember that witnesses are not just there to be leaders and make decisions for the rest of us, they're also there to help keep the system stable by signing blocks, feeding STEEM/SBD prices, etc. So, in this sense, resetting all votes at the same time could be dangerous for the blockchain at any given time.
And if you consider that the days immediately before or after a hardfork are critical times, then it's doubly dangerous to reset witness votes during this period, too. So, we should avoid further damaging the blockchain, all witness votes should not be reset at the same time, at any time.
With that said, I agree that there is a need to clean up witness votes periodically. For example, to make sure that inactive accounts are no longer casting votes for witnesses. After all, why should someone who isn't part of Steem anymore still have a say on who the top witnesses are? And also to get the rest of us to periodically review our witness votes. They shouldn't be permanent, after all.
So, I say maybe just have the votes decay, one at a time. How long this should be, I have no idea. This way, we'll still have a stable blockchain and people will be forced to rethink who their witnesses are, one at time.
P.S. I just re-read the choices and there's an option for votes to expire. I should've chosen that. Lol!