The Revolver Variable
Bullockcm, you've done a great job of looking at your requirements, needs, and wants. Reading your posts I think either a 357 Mag or 44 Mag lever gun/revo combo would be great for you. There are folks who take wild hogs with either caliber, both long gun and handgun. A feral hog is a big tough critter in its own right, so I'd be confident in either caliber for handling black bear - now how much confidence I'd have in myself to handle a bear at close range is probably a bit less
. Like you said, an encounter with one is probably unlikely, but it never hurts to have a gun up to the task just in case.
Now I'd also consider the revolver part of the equation. With a 44 Mag. you're limited to large frame revolvers. A large frame gun (Ruger Redhawk, Super Redhawk, S&W 629, etc) is no problem for most folks to pack when out walking the woods & fields in the country.
On the other hand in .357 Mag you can still get a large frame gun like a Redhawk or a S&W M28, but smaller guns options are available. S&W's 686 & Ruger's GP100 are medium frame revolvers that are easier to carry in more applications, but still very stout guns. The slightly smaller, and now discontinued, Ruger Speed/Security/Service Six and S&W 357 Mag K-Frames (M13, M19, M65, M66) are some of the best carrying and revolvers ever built, and are still widely available on the used market at reasonable prices.
Going down a bit more in size you get into the small (J Frame) S&Ws and Rugers. The little J frame Smiths (several models) and the Ruger SP-101 are excellent 5 shot 357 Mag wheelguns that are very portable. The 3" and longer bbl J-Frames are known as "kit guns", and are still made today. They've been around for years are widely loved for their fullsize gun like long sight radius and small frame weight and size for ease of carry. The 3" bbl adjustable sight SP-101 fits the idea of the kit gun to me as well.
If you've got a gunshop nearby that has a good inventory of revolvers you may want to go there and handle several. Also remember that revolver grips are easy to change and you can find a set that truly fits your hand.
You also said that you wont have the opportunity to test fire a levergun before buying one. If you like the way they handle I think you'll like the way they shoot even better. Best of luck on your gun hunting, and let us know what else we can do to help.