(a) You have me scared now!
.. no need to be scared, per se .. we are talking a low frequency/probability consideration here .. however, far better to have an understanding so that you have the background to figure a risk mitigation process where that might be feasible.
(b) .. which regulation ..
25.149(e) doesn't require wind .. ergo .. none. See, also,
the FTG at AC 25-7A. This is a pretty useful book to read in any case as it gives you heaps of background on how things are done in the certification process ..
(c) all the sadistic sim instructors I've seen
unfortunately, they exist .. however, if the attitude of instructor and pilot is positive and sensible (and the sim fidelity half reasonable), the sim is a great training tool for seeing how things might go when things are a little out of the ordinary.