Having won a raffle and playing with house money, I would ask the question posed above, is this a once in a life time hunt, or can you make it happen again if you wanted to?
Personally, with house money and the ability to go on another hunt down the road, I am not shooting anything I wouldn’t 100% be proud of. Likely holding out for as close to 10’ as possible. If I go home empty handed so be it. I’ll just book another hunt. If this is a OIL hunt and going again is not an option, my expectations would be more realistic and I would be happy to shoot a bear that was a “shooter” for that area based on my guides recommendation.
For the vast majority of friends, family & acquaintances that see the animals we have hunted, they will mean nothing. I don’t hunt for them or for what they will think. I want the experience and the memories. Be selfish, shoot whatever you like and be proud of it. On the Peninsula, the vast majority of good outfitters aren’t shooting sub 9’ bears. Not even a consideration generally so I would think a 9’ or greater is the target size anyways. Now, you may never see a 9’ or bigger bear. That’s just hunting.
I’ll be on the Peninsula in 28’, not with a raffle tag, so I am trying to answer this question as well. Good luck.