@frost-master, I don’t see how he could know how evil they are? It’s not like he and Damien Darhk would likely have crossed paths, and especially considering how long Darhk has been around, many of his really awful allegiances (like, y’know, to literal Nazis in WW2) were well before Len was alive? And Eobard’s from the future and Len wouldn’t know anything about him unless the Len they picked up was after The Flash 1x22, and even then it’s not like team Flash would’ve told Len about EoWells?
And I doubt they’re telling him about their own personal histories; they’re not exactly a forthcoming bunch…
Regardless, I do agree that he’s totally the type to bide his time and see what else he can get out of the situation. It’s very him to watch and see before taking action.
I’m not sure if he’s terrified of his own death. I know that’s @pretzel-log1c‘s position, but I don’t think he’s necessarily motivated by fear as much as he is by the natural desire to continue living and survive, the instinct to see if he can cheat fate, cheat death. I think a knee-jerk reactance to finding out he died and being offered a chance to steal something to undo that? Would be enough to pique his interest. Len will stare down the barrel of a gun, would just as likely say “not interested but thanks for the tip – I’ll be sure not to head on any ‘heroes journey’ in January 2016″ were it not for the fact that his interest is piqued. Not to mention by power and a particularly huge ‘score’ of sorts, a completely new challenge.
All that being said… I really don’t get why this characterization would seem like a reach. All of that is… very fitting to him? And perfectly in line with what canon has shown us?