Oh lord, Connor would be hard. A million directions you could go with that one depending on how closely you wanted to stick to his canon history. But you shouuuld definitely do it anyway! I get to cheat a little because Desmond's already in the modern times, so it's just a matter of tweaking.

Fauxstergo is a great word but YES that's pretty much what I was thinking with that too (poor Desmond, life so hard, etc). wrt factions, it is DIFFICULT because I can easily see him going into either and then making a switch later (either disillusionment with the Circle or 'Hillingdon is great but they're not really helping me stop going crazy'). Decisions, decisions.