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I have never taken masteron so I cannot vouch for its effects on sleep, but I have used winny and it didnt cause me to have any worse insomnia than I normally have. I dont use it anymore though, because both me and a good friend of mine had a major cholesterol swing while taking it. Mine was drastic so I steer clear for that reason.
As far as sleeping pills go, I dont reccomend anyone to take them unless they really have to. Unfortunatally I have had insomnia for so long that I take them frequently. In an effort to limit tolerance to the meds and prevent them from losing effectiveness I rotate the compounds I use. This seems to me to allow me to use them for extended periods and then stop for a while when I dont need them, but individual response and dependence on drugs like benzos and hypnotics varie so much that all other avenues should be tried first. I started out trying everything OTC (like benadryl which only served to make my lay awake with a dry mouth), to herbals which worked for a while, and then finally had to start taking stronger meds such as ambien and valium. The main problem, asside from dependence, that I have experienced is groggyness the next day which I treat with thermogenics. This is a vicious cycle and I dont reccomend it.