I would always rather be safe than sorry, but is there a point where over-caution (or wimpishness) prevents young and inexperienced PPLs like me from gaining experience or dealing with conditions, from building hours and from keeping as current as we'd like? And is therefore counterproductive?
The downside of not flying when you could is that you get frustrated and give up flying, and possibly that you fail to gain experience that might be useful in more critical situations (see below
).
The downside of flying when you shouldn't is that you die.
The mere fact that you appreciate that there is a trade-off there means that you're 90% of the way to getting the risk management right.