I've done a similar trip (out via Mad Gulf, not Osgood), minus a few of the summit loops (I forget which ones now) but it was done in the middle of the summer with more daylight. It's a long day, I was dead tired at the end and would not have enjoyed finishing up with a headlamp. The bottom of Osgood is quite hard on the legs, and when you are very tired and it's dark, that could be the biggest danger factor.
If the weather is perfect it could be a good long day. You can always shorten it as you go along by taking the Edmands Cut-Off to avoid the Jefferson Summit or stay on Gulfside to avoid the Adams climb. Taking the loop around Madison won't save you any time and the trail is much rougher.
Can you do this trip? No way of telling, since only you know how fast you hike. Have you been up in this area before? If not, I'd suggest taking a slightly less ambitious trip to see how you do on the rough Northern Presidentials terrain before starting a death march.
-dave-