I have (only one pair!) of insulated (400 i think). Most of my hunting is a lot of walking and so I adjust socks depending on temps:
warmer (40+ degrees) I will use a silk liner and cotton socks and my feet still get pretty warm usually. YES, I should also have uninsulated boots, but havent' spent the $$ for that.
Colder: under 30* - If I know I'm mostly sitting, liner + nice wool socks. But if walking- wear liner + not as thick wool socks or a blended (Ultimax type) sock from wherever (Cabelas, etc)
These boots have been my most comfy ever and are flexible, but have good grips. Not sure of the exact boot, but close to this: Cabela's 9" Insulated Pinnacle� Hunting Boots with GORE-TEX� Scent-Lok�
Also, if you will wear wool or multiple layers - you probably need a larger size but that depends on the boot. Try them on with the layers you will wear!
Cabelas has the same boot in 7 & 9" uninsulated for about $100. For your description of your hunting, I'd go with uninsulated. Especially if your cold is mainly in the morning or evenings and daytime is warmer. You may be a little cold right away, but shouldn't take too long to warm up your toes(sissy)
You could even pack a couple changes of socks probably (start wtih wool & change when warmer).
