Your buddy's building looks like standard pole barn construction. 2x6 stringers supporting 2x8 rafters. They did adjust the pitch quite a bit. Does his drain well and not leak? I think the lower pitch will be good with screws instead of nails.
I don't like what I see outside of your building. Looks like you've got some dirt work to do to make sure you don't have dirt washing up against the future wall. You might consider a footing and block wall to bring the bottom of the metal up a foot or so, with a french drain to pull the water off. Remember that big roof is going to dump a lot of water in a hurry during a downpour plus water running off the hillside.
From the looks of your existing shop you might do well with less than 8 ft at the wall. A 7 ft wall, or even 6' 8" still lets you do a lot. You need to be very careful where you make the break in the roof if you go for the 8' wall. Wind blown rain can come up quite far on a shallow roof and you will find it is not easy to seal between the sheets of the existing roof and the new roof.
Just not an issue extending a 2x10 rafter. The joint will be close to the end, which helps. If you glue and nail plywood to each side, the same width as the board you will have a joint stronger than the board. I would use 5/8" or 3/4" plywood at least 4 ft long, 2 ft on each board, with the outside grain of the plywood matching the rafter (don't put it crossways). Titebond II would be a good glue. Spread it generously then nail down the centerline of the board then go back and nail an inch or so from each edge, nails about every four inches. An air nailer is nice for this, by the way. If you're going 21 ft with 2x10's you might consider running five ft 2x6 bracing down the center of the rafters to avoid twisting under snow and high wind loads.
Use an online rafter design tool to satisfy yourself that 2x10's won't sag too much for your satisfaction. And be sure to buy structural grade lumber, not common or ungraded lumber. When you look at a rafter design tool it will describe more lumber classes than you will find available.
Where do you plan to buy metal? I can highly recommend Metal Panels Incorporated in Tulsa.
Interesting project!