I don't see why any of Worcester should go un-wired. CSX sunset its Beacon Park-Framingham Plate F clearance exemption, and sunset its Plate F+ (autorack) Framingham-Westborough exemption down to Plate F. The height is completely there. It's only the handful of overpasses between Back Bay and Beacon Park in Plate C territory that pose any problems (with Beacon St. next to Landsdowne Station perhaps the one trickiest). Undercut where you can; coast under dead sections of wire where you can't. It's not hard at all.
Feels like that coasting under the bridges is too easy of a solution to not have problems of it's own. Digging to make room doesn't seem like it should be hard either although maybe it's more expensive than I think.