Sticks, A little story. My wife and I hiked SOBO last year leaving in Mid-June. The same day we left 6 other people started their hike too. There was a group of of four who haphazardly got together before the hike. They were pretty much at each others throats from the start because of different hiking paces, sleeping preferences, meal preferences, you name it. They split up after a few weeks, but never recovered. Not one of the four made it past the halfway point though two of them will attempt the hike again soon. By leaving mid-June to Mid-July you’ll be assured companionship on the trail. You’ll find hiking partners whom you will me able to mesh with very easily. Hell, maybe even on Big K. Blind dates suck!
Katahdin - Get yourself to Millinocket, ME and hitch into the State Park or arrange a ride to the park. If driving to the park, keep in mind only a limited amount of cars are allowed in the park at a time. Beware if it is a nice weekend day. The AT is also called the Hunt Trail up Katahdin. 5 miles up to the summit to get to the starting point of the AT. There are also other, more dramatic trails up Kathadin if you do not want to retrace your steps. I do think they are longer though. Camping is restricted to the Daicy Pond campground for thru-hikers. Space may be available at other campsites due to cancellations, but don’t count on it. Daicy Pond is 7 miles from the summit of Big K. The day after Katahdin you’ll most likely make it to Abol Bridge or beyond outside of the park boundaries.
I urge you to get a Data Book and perhaps even a handbook so you can be aware of mileages, road crossings, hiker services etc, throughout your trip. Hope this helps.
Grimace