A user can have a bad reputation, maybe cause they have a diverse view on certain topics, but they could still very well be trustworthy.
From what I have experienced, I think not everyone has a positive mindset like you. For some people, when they hate someone, they will never take him seriously, they will always treat him like a real scammer.No, you are not to skeptical. The internet is filled with scammers and one is right to be very skeptical with any interaction involving money. The user may have been lucky not to get ripped off in this case, but making financial decisions based on sentiments is never a good idea.
At least you were thinking like me, even if he transacted with me twice, and he sent first, but if he wanted me to send first, to be honest, I wouldn't agree, because I don't really trust him. I'm surprised he trusts me, I treasure it, but it doesn't mean I can trust him. LOL 
Sorry if that guy can read this, but it's true. I'll still look for a safety