Grade crossings were the issue on the Reading extension since it would be prohibitively expensive to eliminate them all. There's something like 13 of them from Wyoming Hill on, which may be the highest concentration inside-128 on the whole CR system. The plan (which wouldn't fly today) was to install pantographs on the cars for a switchover to overhead past Oak Grove so the grade crossings could be safely navigated by the heavy-rail equipment. Part of the reason for the common 01200/0600 car order in the 1970's on Orange and Blue. The 01200's are electrically compatible with 0600 pantographs right out of the box.
Prior to Haymarket-North the Haverhill Line always split off the Lowell Line at Wilmington Junction for its runs (a few rush-hour trains still do this today) and a separate higher-frequency short-turn service ran to Reading. The OL going to Oak Grove mitigated the need for the Reading short-turn, so Haverhill trains were permanently run on that routing. The express track was to be extended from Wellington to Oak Grove with regular 2-track operation past there to Reading. This would've outright cannibalized the CR tracks, which wouldn't be needed because the OL would've been an outright replacement of service with Haverhill trains unaffected because they ran via the Lowell line already. The CR tracks up to Wellington would've been preserved for freight access to the Medford branch (reason for the funky tunneling in that area now). But the rest of the routing would've gone completely over to rapid-transit. It's unlikely this extension could get enough momentum behind it to happen today. Best you might see for OL northside is if the Green Line Medford were to be extended to Woburn/Anderson RTC (possible...when you consider the Lowell Line ROW is wide enough and could get a full reconstruction in the next 30 years if it actually gets enacted as a high-speed corridor to NH/Maine and Boston-Montreal like Obama wants, and there's only 2 grade crosses in close quarters at West Medford that would need elimination). In that case the alternate proposal for the current extension, branching the OL at the portal to follow the Lowell Line tracks in-full instead of branching from the Green Line at Lechmere, could very easily get enacted with a short and cheap amount of construction to the Lowell ROW snaking around BET...thereby relieving the GL of a super long-distance run and relegating its northside presence to the Union Sq. branch and future inner-city ring routings. OL actually would've been the better way to do the Somerville extension from Day 1, but given the massive delays it proved path-of-least-resistance to just poke the GL out there past Lechmere.
On the southside the extension would've followed the Needham Line from Forest Hills to West Roxbury, taking over all the local stops, then peeled off on the ROW of the former NH RR Needham and Franklin line Dedham bypass (last revenue service: 1941) to Dedham Center and the current site of the Dedham Mall. The T still owns the land for this ROW, which is
very clearly visible from satellite from the conspicuous place at West Roxbury where the Needham line makes the sudden curve, and is then traced by the side streets in the area until it runs into the center of the Mall (which probably would've been redeveloped to accomodate a new terminal if the extension were done during the SW Corridor relocation). I don't know if the West Rox-Dedham leg could happen today since there's NIMBY problems in the residential area it would travel to (they won't even let a trail get built on the ROW) and there'd need to be land-taking. The T has tried to no avail to sell off the land for trail conversion, with no takers. But there's an easier way to reach Dedham Ctr. anyway with the Fairmount/Indigo line having easy extension potential past Readville on the much better-preserved Dedham Branch RR (which the T still holds the RR operating charter on, unlike the West Rox-Dedham ROW where it just has the land with the charter getting abandoned long before it purchased the ROW).
I still think the West Rox extension needs to happen someday, and honestly should be a much higher priority than the non-existent one it now is. It's absolutely insane how many buses go out to Rozzie Square from Forest Hills, so the transfers would work vastly better if rapid-transit were extended out and kept all that extra bus traffic off Washington St. If the eventual Indigo upgrade of the Fairmount brings Hyde Park more-or-less into the quasi- rapid-transit system, then Rozzie and West Rox are the last 2 Boston neighborhoods 100% unserved by any rapid-transit access, so there's a glaring neighborhood equality need. And the Needham Line, despite being single-tracked today, has the ROW capacity to handle 2 OL tracks and 1 CR track (albeit with some land-taking needed around the stations because of encroachments). You'll notice that all the bridges on the line have 3-track width abutments even if the 1980's-rebuilt decks on those abutments are only 1-track width. The line used to be 3-track to West Rox and only narrowed after the former junction there for the leg to Needham Junction. So this extension wouldn't cannibalize the Needham/Millis CR routing at all if the intermediate CR stations between Forest Hills and West Rox were eliminated in favor of the OL. And there are zero grade crossings on this route unlike the northside extension. Wouldn't be an overly expensive one to do save for the encroacher land-taking, and the OL has the capacity to extend (could even utilize the northside express tracks at rush hour if needed), so I don't know why this is never on the radar screen. I think Menino's home base in Hyde Park is keeping support artificially muted with a suburban NIMBY mentality in the westernmost neighborhoods. We know how anti-rail he is, and extending the OL to West Roxbury would put much higher impetus for Arborway restoration with Forest Hills no longer being a terminal and the E taking on a crosstown route importance for commuters from the west. Don't underestimate how much restoration politics are holding back the OL. In the natural order of things, though, the pre-existing rubber-tired transit patterns in those two neighborhoods practically scream bloody murder for it to happen on quasi fast-track priority.
This is where DMU's can really help accelerate a route's conversion to full heavy-rail rapid-transit. If you upped the headways on the Needham Line significantly by replacing locos with DMU's the ridership explosion from Back Bay/Ruggles/Forest Hills transfers getting to/from Roslindale and West Roxbury would make fast-tracking the OL extension bloody obvious in no time flat. Another reason why the T and city are treating the DMU halfway mode with derision. Needham Line would probably be the #2 line to convert to those types of trains after Fairmount because it's the other near-total inner city CR route unlike the others. But, again, in addition to that creating self-fulfilling demand for a proper OL extension it also loses the T/city a lot of control on repressing Arborway restoration because of the crosstown aspect, and also brings about the specter of increasing demand from Needham commuters for the long-envisioned/never-executed Green Line Needham Junction spur off the D at Newton Highlands. Probably a reason why the Needham Line doesn't make use of the other half of its semi-active trackage to Newton Upper Falls and Highlands...not even the dead-obvious and dirt-cheap 1-stop extension to Route 128 park-and-ride they ought to have done decades ago at TV Place/Exit 19. I really, really hope whenever Menino abdicates the throne that somebody a little transit-friendlier gets into office and uncaps the artificial lid on this one.