I travelled down the same road as you are on recently, and already have a TC Encore with a 20 gauge rifled slug barrel and a Leupold 1-4x (deadly accurate with the Winchester Supreme slugs). I hunt out of a treestand most of the time (Central Upstate NY), and wanted a handgun.
I bought the Ruger Super Blackhawk Bisley Hunter in .44 Mag ($500 or so new, if you shop), and originally had a red dot on it. I ended up not caring for the red dot as the lack of magnification, at least for me, made longer shots difficult, and I am use to telescopic sights.
I replaced the red dot with a mint condition, used Nikon 1.5-4.5x scope I got on ebay, and am very, very happy with the combination. Many don't like the lok of a scoped handgun, but I think mine looks awesome: stainless gun, silver scope. More importantly, it is much more accurate than I can shoot it right now.
You might consider the gun I have to start, then add a TC Encore with a 7-30 Waters barrel, or some light rifle caliber that will let you truly reach out and touch past 100 yards, should you have that kind of range in your hunting grounds.
Best of luck to you.