I can't really speak in personal terms about weight cutting as the most I ever pulled was like 5 or 6 pounds at the start of the week up until match time, and that was still generally eating whatever I wanted up until the day of.
I actually spent my last year and a half or so of wrestling trying to gain weight. Not to make you all feel bad or anything.
I did have a buddy though on my team, tough kid but for his first three years he cut way too much weight, and was absolutely miserable doing it. Our senior year he wound up going 171 while walking around at about 169 and made the state finals.