Ahoy! Roof Experts

[RHD]

Personally, I don't like the way it looks. The stick builld transition between the original roof and the new trusses [if they are the same slope] is not that difficult. We used to make a ridge board cut square on the new truss end and a #/12 cut on the old roof, level it and nail it in. The cut "rafters" that have a ridge cut on the uphill end and a COMPOUND cut on the bottom. All can be done with a portable skill saw.
Snap string lines from the ridge for guide and nail a flat 1x8 onto the old roof right over the shingles. Cut right and left sides to match for lengths and make sure they are perpendicular to the ridge. I'll try and draw and post something if time.