Hey man,
Check out Wazkelly's swampy caster. I think it may be the look you are going for.
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So I think I'm going to go with feast Watson black for the top. I want to darken the fretboard a bit what due would be best for this and is there anything to worry about with the inlays (triangular ones btw)?
If you want a darker board, then unless you want it really black, I'd first try wiping it with lemon oil. It's the standard oil for conditioning rosewood boards. Wipe some on, and depending on how dry the board it, it may soak in over a few minutes or a few hours. Once it's dry, apply some more oil. Keep applying it until the board stops soaking it up, then wipe off the excess. It should now be considerably darker. Lemon oil won't affect the inlays at all.
If you want it a lot darker, then some people here have used leather dye pens. This can stain the markers (though it should polish off if there aren't any small cracks in the markers), but it's best to try and mask them if possible. Probably easiest to do by covering them with clear tape and then cut round the markers with a sharp craft knife or scalpel. The tape will probably leave some sticky residue (unlike masking tape) but you can easily clear that off.
Got some more stuff for the kit today
Attachment 18913
What would be the best way to cut the headstock? was thinking kind of like a strat headstock.
This works well for me
Attachment 19310