I might be having partial success with this idea. As of right now the seven administrators (mayor, manager, broker, bookkeeper, militia commander, chief medical dwarf, guard captain) and the baron (who was appointed, not sent) are all armed and armored in steel gear (all superb or higher). They are actually my starting seven (other than the guard captain), and after fending off 15+ years worth of enemies they've all reached legendary status in their respective weapons (short swords, spears, and crossbows). They go about their usual tasks while fully equipped; they never take any of their stuff off, even when throwing parties.
However, I am having trouble making my miners behave the same way. For some strange reason I cannot fathom, whenever I designate squares for mining, the miners (despite having the pick equipped as a weapon) run around the armories stripping themselves of all equipment and then pick up another pick before going down the shafts. After the designation is satisfied, they throw away the pick onto the tile they are standing on, run up to the barracks and rearm themselves. Sometimes they ignore this part altogether and simply drop the pick and move around.
On a side note, for causes unknown the pick is listed as foreign in the equipment page. Perhaps this is why the miner squad is not functioning as intended?
I will experiment with other militia settings (especially having the woodcutters designated as axedwarves). I will report back with further findings.