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I may be moving to NY. yes, I know what that entails. But I would/will go with whatever I end up getting in a revolver. I love a 357 and how it shoots, so I would probably go with the same in the lever gun for commonality. I would do more plinking than anything, and being about to shoot soft 38s out of a rifle is a hoot.
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As to caliber, the 357mag is a very versatile caliber. Commercial ammo is readily available in 125 and 158grn loads from about $12 per box vs the $20 per box for 44 mag. If you handload the price difference between the calibers is less, however, you can make up a wider variety of loads with the 357mag. From 90grn up through 125, 140, 158, 180, and even 200grn light or heavy loads, you can set up for plinking, light game, and even 100yd deer sized loads.
As to the Henrys, I too find that their excess weight and lack of a side loading gate, make them a non starter for my collection. I have 2 Ubertis in 45 Colt, a '66 carbine and '73 rifle that weigh as much as the Henrys and they are a bit tiring to lug around in the woods. I also have 2 Rossis in 357mag, a 20" carbine and 24" rifle and they are much lighter and more fun to carry.
Finally, the 44mag in a levergun is a great, hard hitting caliber for short range shooting. Their 240 or 300grn bullet loads are well suited for meat getting in the woods. The 357mag is also a great caliber for a levergun. It's greater versatility, lower cost, lighter recoil, and much longer range (I shoot my 357mag rifle at steel plates at 300yds) is hard to beat. In my book, it makes it a better choice for an all around shooter where you may want to plink, hunt small game, and with heavy loads, take medium game.