@Brian Golden , somewhat uncertain on answers, but these are some of the same questions we're looking at as well in weighing a potential future migration. My understanding (which I'd love to hear from others if I'm wrong on) goes like this:
1) Subset migration. There's an answer on this I see already posted, but you should consider carefully what problem you're trying to solve here. Are you intending to have a transitionary period where your company is split on DC and Cloud?
2 & 3) On the "problem you're trying to solve" I'm guessing you're thinking of continuity support for incoming links. From our discussions with Atlassian (which I hear second hand at this point) it sounds like Atlassian can provide a mapping of old to new. Our theory right now is that we can make the redirect facility to provide that continuity, but my understanding is that this is from our IT group, not Atlassian-provided. You may want to check in on your local resourcing.
4) I get the impression that the idea is that if you don't want to migrate something, then clean it up ahead of migration. That would be deletion in this case, as you might have read about the problems Atlassian currently has with migrating Archived items.
5) Talk to the add-on vendor.
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