I know nothing about the Ozark Highlands Trail. For your time frame and distance, you might consider doing a part of the Florida Trail. I would think that some of the CDT in New Mexico might be fine in that time frame; it was early November when I finished my hike in NM and conditions were fine, albeit of course the amount of daylight available for hiking was reduced, an issue you likely face regardless. You could likely carve off a SoCal chunk of the PCT too, south of Kennedy Meadows (perhaps Tehachapi/Mojave) on the north end, and north of Mount Baden-Powell and Fuller Ridge (i.e., so well north of Idylwild) to the south.

All things being equal, my preference for winter hiking would be to find places that don't offer a whole lot of snow! But the Ozark trail might be fine, I just don't know. Whiteblaze has a "other trails" forum where you might get more feedback if you don't find it here:
https://www.whiteblaze.net/forum/forumdisplay.php/105-Other-Trails