Well, I think most people would prefer the Essex routing on instinct. We've hashed out again and again why that probably isn't feasible. But obviously in real life, they would study several options and hopefully select the one that provides the best bang for the buck.
I was a die-hard supporter of the Essex routing for years. It wasn't until I actually started playing around with what could go where that I realized what a boondoggle building it would really be. The proposal along the Pike is really a rehashing of the Stuart Street Subway proposal that was floated by the MTA for years.
ESSEX PROS:
-Straighter alignment (~1/2 mile Boylston-South Station)
-Provides a walking connection between Boylston and Chinatown stations (early Orange Line connection to avoid overcapacity Park St)
ESSEX CONS:
-Does nothing to address Boylston subway capasity constraints or Copley Junction chokepoint
-requires deep-bore construction near historic buildings through unknown soil conditions
-Essex is barely wide enough to fit an island platform + 2 tracks, and they would have to be mined out
-Have to get over/under the Dewey Square tunnel
-Post Office Square extension provisions are likely inadequate for the necessary grades. In all likelyhood the new tunnel would have to start at the old portal by the Public Garden, making it closer to 3/4 mile of new, deep-bore tunnel
-No possibility for connection to Dudley Square service (assuming the retarded under-the-common bus loop doesn't happen, WHICH IT SHOULD NOT)
PIKE PROS:
-Reuses existing infrastructure through the historic core (abandoned Tremont St Tunnel)
-Cut-and-cover construction due to known soil conditions along Pike trench
-Provides walking connection at Tufts/Bay Village
-Provides a southbound looping point after Government Center. Currently branches coming in from the west can loop at Kenmore, Park, Gov't Center and north station, allowing short turns and emergencies to be handled reasonably well. Trains coming from the north can currently loop at Gov't Center and Kenmore/Blanford, and that's it. This way you can turn a train and still let it hit Park St. That's huge.
-Allows a light-rail extension to Dudley
-If at full build (the Copley-Bay village and Brookline D-E connector) you avoid bottlenecks in the Boylston subway and can take Copley Junction out of service, fixing many of the current issues with the existing subway.
-If at full build, potential to connect the Green Line D, E and potential Needham branch to Back Bay Station.
-It is the North-South connector. Lack of a one-seat subway ride is often toted as a big problem. This solves that.
PIKE CONS
-Longer routing (over a mile vs ~1/2), although it would be fast track ~40MPH. Historically the abandoned tremont section was the fastest part of the subway, operators would let it rip.
-Issues routing tracks around the South Bay interchange, although no matter what getting around 93 is an issue with any option.
That was basically what I started seeing as I was making the linked map. Feel free to add to the list.
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As for OL to Rozzie.
Yes. It should be the beginning of a phased replacement of the Needham Line.
1) Extend OL to Roslindale. Partner with a developer to redevelop the station+ parking lots. One MASSIVE below grade parking garage below the current lots+station would replace the spots 1 for 1, plus add parking for residents. Retail where the current lower parking lot is, busway + drop off where the upper parking lot currently is. 2-3 floors of residential above. Added benefit: Station is covered, and free. You could also reconnect South Street with itself, which should help with traffic.
2) Stop-by Stop extend the Green Line to Needham Junction.
3) Close the Needham Line, extend the Orange Line to West Roxbury. Build a new terminal for buses and a park-and-ride behind the Home Depot. With any luck this would capture a lot of the traffic from Dedham-south using the parkways, and could also spawn some TOD where Savers and all that stuff is.