I've driven a good sampling of 98-2006 Sterlings. With the exception of a handful of old Freightliners and new Volvos with sleepers for Team Runs they are all Con-Way has.
You're effectively buying a freightliner with in a different body style.
Con-way specs our tractors super cheap with 7 speeds.
The AC units in our older tractors tends to go out; even when they are working they are weak and can't keep you cool when its 100+. The height adjust knob on the seat tends to break off; On about 1/2 of the tractors at my barn you have to use a pen or key.
The ride quality is crap. However my perspective is limited as the only other equipment I've used is our freightliners and a handful of Rental tractors.
With Sterlings you sit higher and a bit foreward compared to most other trucks. They have good visibility and a tight turning radius. I get into our freightshakers and I feel blind.
If you live near a larger Con-Way terminal with a shop I'd try and pick the brain of a mechanic.