i really like my Cabella's Outfitter boots, 1000 gr insulation, goretex. a little more insulation may be better. I bet those 40$ boots are junk, they hurt your feet? I walked a lot of miles deer and elk hunting in my non insulated Outfitters this fall, almost brand new. I walked atleast 8 miles in one day with snowshoes hunting coyotes in my insulated Outfitters, feet were good. These boots are 6-8 yrs old, still don't leak. My old Rockies would leak after 2 seasons, usually.
For sure get rid of cotton socks, I only wear wool blend ones in the cold weather. Make sure they have no seams above or near the toes, the cheap socks might be like that, will cause trouble on a long day.