Akramitis,
Trying to understand - does he want to backpack in and portage his canoe the entire way?
If so, he could probably just take the Ward Brook Truck Trail from the gated area just past the TH to the Sewards - Assuming he would be carting it in. - It about a 10-11 mile very easy road walk, and while it is private property for the Ampersand camps, I don't think that as long as you follw the WBTT and don't turn off and go to Ampersand Camps, anyone would give you a hard time. I have biked in that way 4 times without any problems when I wanted to get in and out fast (I used to maintain a couple of L/T that way, and due to some of the horsepackers, there was usually a lot of trash to be carried out of the L/Ts) and you can make good time carting 10 miles on the road vs carting 7 miles on the trail from Upper Works.
If your friend is thinking of paddling in, Check in with Redhawk at ADKforum. They just paddled in from Henderson Lake through Preston Ponds to DH. I understood it to be a rather grueling portage.
I would say for your first time there, just backpack in and do some exploring. The Indian Pass/Preston Ponds Trail from Upper Works isn't that bad. IIRC, it was about 7 miles and is certainly more enjoyable than the road. I'vebeen through there twice and find it a nice alternative to the WBTT