Almost reached the top during (snowy) March of 1997 via Old Baldy Trail. No snow below Josephine Saddle. Approach to Baldy Saddle didn’t require snowshoes, though my hiking partner kept insisting we should’ve been carrying ice axes rather than hiking poles. Actually the conditions weren’t particularly treacherous; much better than the freeze/thaw cycles of later in the season which create an icy runway in that stretch.
Ultimately we didn’t summit due to very deep snow around the cone and the labor of postholing. The trail up from the saddle wasn’t followable and I believe we tried a direct ascent through the forest. With much of that forest now burned away, the lay of the land (and potentially the depth of snowpack) could be easier to negotiate.
Conditions were fairly mild up high, as we chose a sunny day without wind. Which timeframe (Dec-Jan-Feb-March) is most challenging would depend on when the snow falls and how long it sticks around. Other factors can be controlled for.
blisterfree