Tortuga:
1. Should I aim for 500 cp characters at the end or 1000 cp?
500 ought to be a decent "super-human" but not "a super" level. Especially if you're not allowing Cinematic traits.
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That 1 point in chemistry/5 you learned in the 1800s probably won't stick around forever.
Also keep in mind that the Chemistry bought in the 1800's is what, TL 6? Modern area is TL 8, so it's not just degradation with some skills, it's advancement of techniques and methods.
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2. X points per year skipped? A set sum between adventures, with a larger sum between eras?
That's probably the easiest.
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Allowing disused skills to be refunded/traded in for new skills?
Yeah, that wouldn't be bad, especially if the Character start in pre-metal working eras. You could put a limit of X number of skill points may be traded between eras.
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Increasing levels of Reawakened to access skills you've largely forgotten?
That's an interesting idea.