That's the thing. If I know I'm gonna use a rest, I might as well get a 14" .460 Encore.
At less than 30-40yrds, I'd probably hate it. That's when I'd want to be able to shoot free hand.
Which brings me back to the 2 gun idea....
I can only share my experiences. I use a 8 3/8" S&W M57 (41 mag) with iron sights or a Ruger SRH in 480 Ruger with a 2x Leupold scope.
I'm certainly okay to shoot to 75 yds, certainly 50 yds with my M57. I shoot the SRH better with the scope, but it is much harder to shoot without a rest. The scope makes sighting easier, but it also shows you very well just how unsteady you really are sighting with a handgun. Hence.. the rest.
I don't consider the M57 particularly front or barrel heavy. The longer barrel makes it easier to sight. My SRH has a 9.5" barrel and it is a handful, but I wouldn't call it barrel heavy at all.
The purpose of the rest is to allow you to make a better shot just like most people shoot better from a rest on a bench versus holding a gun in their hand. As was mentioned, you owe it to your intended quarry which I assume is probably a whitetailed deer that you make a good shot when you take a shot.
There is something to be said about a Contender or Encore for practical usefulness during traditional big game hunting because for me in practice the SRH is a big revolver and it is not practical to carry another firearm hunting unless I am perched up in a tree stand/elevated stand. In that case, you can probably use both and choose the gun you want to use based on the circumtances of the available shot. Rifle or big handgun or iron sighted handgun... But deciding which gun to use can also cost you a shot, so my advice is to decide before you go out.... I am going to use this gun period and hunt accordingly.
I think you are fooling yourself regarding shots of over 100 yds. It can be done, but you will need to practice a lot
to be reasonably proficient with the gun at 100+ yds. It is not like shooting a rifle.
I am in the process of acquiring another revolver (6.5" barrel) for hunting. It's a BFR in 480/475. It is not barrel heavy. I don't know if I'll mount a scope/red dot on this one until I shoot it a bit. But I would prefer to leave in iron sighted. It will take some practice to be able to hit a 6" paper plate at distances over 50 yds. I just hope it is more comfortable to shoot than the SRH.
(Two Gun approach)
The two handgun approach is okay, but not particularly practical in the field unless you are hunting from a stand. You certainly will find the guns heavy after a long walk to your "spot".
I started out carrying both a revolver and a rifle. I wanted to hunt with the revolver but I also didn't want to miss a reasonable shot. Hence when I had both with me, I always chose the rifle. From that point on, I decided if I was going to hunt with a handgun, then I would only have the handgun with me.
Shoot a bit and this belief about using or needing a rest will fade away to the practical aspects of hunting. You will choose a rest every time if you can. I can only take "quick" shots without a rest with the SRH. When I say quick... that means... there's a deer and a shot and I had better take the shot quick or it won't be there. Pull up and squeeze the trigger quickly or I would almost certainly miss the target or make a poor shot.
I think you would be doing yourself a favor to hunt wood chucks (or something similar) with this hunting revolver to get you comfortable as to what your shooting capabilities really are.