Some posts are incorrect so to help clarify a few of them.
Taken from the IDNR web site:
For handguns, a bottleneck centerfire cartridge of .30 caliber or larger with a case length not exceeding 1.4 inches, or a straight-walled centerfire cartridge of .30 caliber or larger, both of which must be available as a factory load with the published ballistic tables of the manufacturer showing a capability of at least 500 foot pounds of energy at the muzzle. Note: There is no case length limit for straight-walled cartridges.

No difference in strength between your original Contender and the newer G2. Barrels that will fit one will fit the other. Some say the newer G2 is stronger because of the extra metal on the sides, but TC still lists it as the same pressure limit as the original Contender so I go with that. There are differences like the G2 doesn't have to have the action opened to re-cock the gun if the hammer is let down, etc.

Also fourbore stated above that the 300 Blackout is a bottle neck and won't make the cut. False...the 300 Whisper/Blackout has a case length of 1.368" with is under the required 1.4" length and is perfectly legal.

A 100 yards is easily doable with practice. Handgun scopes require a steady hand or you will lose your sight picture so practicing is paramount. I would suggest a quality field rest like a trigger stick/bog pod and a sling for your contender to help steady your shot. Practice, practice, practice it is the only way to build confidence in not only your gun but your ability to make the shot.

Get the 45 Colt since you are leaning in that direction as it will do what you want and can be hand loaded from mild to above 44 Mag performance. If you don't hand load then Buffalo Bore makes great hunting ammo that would fit your bill.

I have been a avid handgun hunter since the mid 80's and hunt with revolvers to Encore/Contenders to custom XP 100's.

Lastly join the Specialty Pistols forum, there are a great bunch of guys over there who shoot and hunt with Encore/Contenders, XP-100's, custom revolvers, etc.