What a wonderful post! Just wanted to chip in here:
The answer to this will be experiential, but just wanted to point out that, being naive does not mean going around believing what everybody says and being unable to lie or deceive people when it makes sense to do so. Viz.:
RESPONDENT: Do you live a moral life? If so, why?
RICHARD: Being free from malice and sorrow, I am automatically happy and harmless. Thus I have no need for morals whatsoever. Morals are designed to control the wayward self.
RESPONDENT: Would you lie, cheat and steal?
RICHARD: If the situation calls for it, yes indeed. Whilst some semblance of social order prevails, such actions as stealing are not necessary. The government bureaucracy however, being adversarial by nature, occasionally calls for some creative massaging of the truth regarding my life-style. [link]
Believing what everyone says (including deceitful people) and being unable to deceive them back when prudent to do so, is how a child goes about the world, because they don’t know any better. However, having more experience in life, you do know better, and this experience doesn’t go away just because you are more sincere and naive.
I actually have found the opposite – the more clean and clear and sincere I, myself, am, the easier it becomes to read other people and spot when something isn’t quite right.
The way I’d put it is like this: actually the ‘normal’ way of going about the world is one in which I have many and various buttons to press, and particularly cunning people can find and press them in order to hoodwink me. With fewer of these buttons, that just doesn’t work… and having gotten used to just always wanting to find what the facts are, and refusing to accept things which don’t make sense, it’s just very easy to spot when something doesn’t actually add up and then see why it is the case.
So in other words I wouldn’t worry about it, I encourage you to go ahead and try it, incrementally so even, just a bit at a time you feel comfortable with and see how it goes 
Cheers,
Claudiu