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I personally wouldn't go below 250 grs if bears are in the mix, and I would prefer a 300. Sierra's 300 comes in a box marked "Hangun Use Only". I find this a bit odd what with Sierra's claim about these bullets offering exceptional penetration in game - and it is listed in the rifle section of their loading manual for the .44 magnum, but not for the .444 Marlin. Perhaps the box should of been marked "not for use with .444 Marlin. So my black bear load would be the 300 Sierra - backed by 20.0 grs of H-110 or Win 296. I've used lots of different powder in a number of .44's and have settled on H-110 and Win 296 as my favorites.
I tried the 300 gr. Nosler and found that they placed the cannelure so far forward that I couldn't seat the bullet deep enough to crimp properlywith a max load of either powder.
If you are interested in casting Lyman #429640 - a 270 gr flatnose - looks quite good.
For deer you may prefer a lighter faster expanding bullet between 225 and 250 grs. backed by 25.0 grs of powder for the 220 gr bullet and 23.0 for the 250 gr.
One last thing...if you are going to begin reloading purchase a loading manual - for your purposes I would recommend the Lyman.
What 165gr? Who told you that? Lighter bullets will travel faster and therefore expand more, btw you can push a 180gr at almost 1900fp from a 8in barrel, with a rifle it will be even more....
For hunting always go with a heavier bullet, it may have less energy but it will penetrate more
Actually I've been lobbing 240gr bulk winchesters (NOT REMINGTONS!!!!) with 25 grs of H110 ,killing those exact critters of which you speak and been very pleased with performance.