I have some thoughts on this,

First a little history

When I moved to NC in 97, I did not know anyone, knew nothing about the hunting or anything of the such, But I knew that I was going hunting, as i had done every season in Fla for years. So I contacted an outfitter,charged me $500 for three days of hunting and I went around my birthday(it's how I remembered the dates). Never shot anything with a rifle at this point but owned them for years, had several bowkills under my belt. Anyhow hunted the first day- no deer sighted, hunted the 2nd day killed a large 9 point, the 2nd morning crossing a road, threw the rifle up put the crosshairs on him bam, the next day and half - no more deer sighted - this deer is mounted on my wall-

Now fast forward - as I became more familiar with Land and hunting strategies my focus became on learning about the deer and determining how to set-up which landed me nice bucks in 04, 05, 06 (my biggest with anything-bowkill) I also took a nice buck in 06 with a rifle. So two nice bucks in the same year.

So what does all of this mean
Well the buck I got in o6 is a lot more special than the outfitter buck becuase I found him, I did the work and i got him with my bow

Now to answer your question,
I want to go to the Milk river and hunt whitetails and also to North Dakota- the reason I haven't is I haven't found someone to go with- so I think my answer would be the trip would be worth it for the companionship, but the trophy would not necessarily mean anything more to me than the ones I have taken here - I also have a hard time spending the cash - when a big ole slickhead here means a helluva lot to me