Peter,
Yes, there is a difference between awkward and challenging! While it may not be the ideal for most around here, I try to minimize awkward, because hardly anyone really likes it (when it happens to them, if it happens to their opponent, so much the better, LOL)
Of course, there are awkward lies, which to me is part of rub of the green. And, I have always allowed or graded fw areas at more than the minimum, which gives a slightly different lie every time you play (i.e., 3-5% rather than 2%, which is close enough to flat for most to not notice the contour of the lie)
But, I sense the question is about awkward shots, like a long iron off a downhill sloping lie to an uphill green, or due to crosswinds, having to aim over water to hit a green or fw. (i.e., the physics of golf reduce greatly the chance of success on a well struck shot. Those are beyond awkward, IMHO, and maybe even outside the realm of a fair but uncomfortable challenge.
Having crosswinds from out to in, i.e., on the low side still create a challenging shot in judging the drift controlling shot pattern, etc. I mean, you still have to hit a green in a cross wind, which is hard enough (and, BTW, I would probably also use a pretty wide green. My mentors once did a skinny green in a crosswind and were roundly criticized for it) for anyone.
However, a conservative miss turns into a bail out, not a water hazard or O.B., and the resulting 2 stroke penalty (maybe one if truly a lateral hazard. I don't go out of my way to create any shot that is purposely awkward, but then again, I can't know every degree of awkward across a range of players, nor does the land always allow theoretically "perfect" comfort conditions, so a few of them probably creep up on every course I have designed.