I really don't see the need for them to tie things in with the first 20 films. It would essentially make the reboot (as weak a reboot as it is) pretty much a pointless exercise. What they need to do from here is to just craft some good, solid original stories, taking their cues from Fleming when necessary and/or possible. The only previously used element I think they need to revisit at some point is Tracy, but I don't think that necessarily has to be done within the confines of a remake of On Her Majesty's Secret Service. It could easily be done within the confines of a completely different story and still have the same effect. That's the only already used element from the first 20 films that I think needs to be revisited, albeit not any time soon. Other than, it should be completely original from here on out.
Great points. I think a lot of us (myself included) drift between thinking of 2006-on as a reboot or a prequel. And I'm not even sure EON have a long-term plan other than "CR shows Bond at the start of his career." But to be fair to EON, I've only ever seen Babs & Mike, and Campbell et al, refer to this era as a "reboot" so maybe it's just us fans who project the idea of it being a prequel, and so therefore having to make sense in even the loosest of continuity.
As great as walking through the padded door (or should that be cell, the more we all think about it!!!) undoubtedly was, it doesn't necessarily mean we're at the start. Figuratively we've reached EON-Bond as conceived in '62, but literally and chronologically maybe not.
Only the next couple of films will signify if the end of SF is everything coming together, or truly a new start.