Biggest regerts:
ALPS Outdoorz Commander pack - tried getting in cheap with a decent meat mauler...it's not decent.
Leupold VX3 - Love the scope, love the adjustments and the CDS. Hate that I didnt bust out the few extra bucks for the Adjustable Objective
Kuiu Yukon gloves - bought these for subfreezing conditions. Hands were terribly cold in high 20 degree dry weather
Wasted money:
Alaskan game bags - bought these to help me make it through the first hunt season, made the jump to synthetic bags midseason and didn't look back
Bear spary - lost 3 cans this past year from having it slip of my belt or pack belt as some point
Kuiu bino harness - worked great the first season, but the elastic is now stretched and doesn't hold them that well, upgraded to Marsupial this year
Surprised:
Danner Pronghorns - Bought these at Cabela's $100 of retail. Made it through a season and half. Well over 100 miles in them as well as a elk packout from 4.5 miles back. They leaked this past season, but not terribly. I seam sealed them this year to hopefully make it through one more season