I hiked the northern 1/3 of the trail in 2008 and the southern 2/3 in 2009. Solo is no problem and the trail is very well marked.
Definitely no need for bear canister. Last year there was a pesky bear hanging around Seth Warner Shelter (southern most shelter). Green Mountain Club put a metal box there for food storage. If box not there, just hang food in tree.
I hiked with a one person tent. I did not use it at all on the northern 1/3. Out of nine nights in shelters, I was by myself for six of them so overcrowding was no problem. On the southern 2/3, I used the tent three times. Once because the shelter was full (Seth Warner), and twice because at the end of the day, it was too far to the next shelter. I did pass some other shelters that were full in 2009. The issue is more traffic in southern 1/3 where AT and LT are the same, and groups from boys/girls camps that are out on the trail in the summer.
If convenient for your trip, I highly recommend staying a night at the Long Trail Inn and Nye’s Green Valley Farm in Jeffersonville. The owners at both places are outstanding hosts.
My favorite shelters were Skyline Lodge and Spruce Ledge. Relatively new shelters with great views.
Have an outstanding hike!
D6