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The Fairy seems by far the best starting position. It has the opportunity to get a bonanza of 30ish cash around turn 4. That's an enormous amount.
Good player will have the point booster by turn three: First turn upgrade to level 2, having avalaible for the following turn 2 blue and two green cards; Second turn upgrade to level three and buy a runestone to reach level four.
In my experience the fairy is no better than others. It start strong, and usually is the first to reach 10 vp. Anyway 30 production points are not enough to mount such a better production to compensate the malus for being first, so often the fairy will slow down. Furthermore other players could decide to go for the 9 mages big cards in better times, when masks, chalice and sentinels come out. In that time the booster is more useful.
The real fairie advantage is the possibility to choose almost unopposed (mage apart) the strategy. You can collect two, three artifacts, or start a second knowledge path.
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The other quirky card is the Tomcat Sentinal. It's always worth 17 VPs in the end as long as the purchaser knows to convert all his factories (umm, gems) to Ore factories on the last turn. This is not hard to do. So the first purchased sentinal is worth 17. Most other players can get 11-12 or so out of the best sentinal for them, but some may only be able to get 9 points.
In reality the Tomcat can give less than 17 VP. You have to sell gems to create room for opals. If you sell sapphire it means your production is quite low, then it will be a contested auction.
If you sell better gems, you lose 2VP for each one gaining just 1VP for the opal plus the bonus.
This means that if you have a character using just top gems, your sentinel net score will be 11 VP. 6 VP bonus is quite easy to reach with other sentinels as well.
Tomcat is very good if you have mixed gems, and even better if you can safely convert your gems to opal knowing that the game will end. If not, your last turn will be a nightmare. Tomcat is very risky for the leading player. It is a sentinel I like a lot for helps player in back position to come back in the game. IMO it is less useful for a leader.
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The third issue is that the Druid's starting position seems lame. He'll come back with a vengeance in the end game, but he rates to be near the back of the pack in the early game, and in an exponential economic game, that's a position from which it is very hard to recover
Druid is the most difficult character to play, I try to never give him to newbies. It’s a sort of diesel, the more the game last, the stronger he is. Probably this is the role most influenced by other players strategy.
I have seen him have his fair share of victories, and as such is not disadvantaged. The downside it is that an optimal strategy means that for 7 turns you will enjoy less, as you could not use resources for nothing else than knowledge.
I've never played Outpost, and given your comments I'll try if I look somebody having it.