I have read here in the forums before that the Park Street loop and associated S-curves leading into and out of the loop are the tightest curves on the system and the limiting factor overall. From what I recall of a few wheel-screeching trips around the Kenmore loop, it's pretty tight up there too.
Not to shift focus, but since Toronto was mentioned, they have their share of close clearances underground as well. The underground curve at Queens Quay is very tight both in radius and wall clearance, and the Union Station loop is so tight that there are warning marks and tactile on the station platform (which is right on the curve!) extending several feet out from the rail to keep people away from the wide swing of the cars around the loop. My photo:
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One of the things that is a design challenge for Boston is that the Green Line is neither what can be called true, modern light rail (which at its most evolved is not much less than full rapid transit), or a traditional streetcar system (like Toronto still is). The Green Line straddles both worlds, and that's where the trouble starts when it comes to equipment design. Fully low floor, multiple-articulated streetcars like what TTC has acquired might fit in the clearance diagram of the subway and negotiate the snaking curves easily, but they are not well suited for high speed private rights of way such as the Riverside Line, or presumably the Mattapan Line and Somerville/Medford extensions. You think a Type 7 has a lot of lateral motion? Add a few extra articulations!
Cars that are designed for higher speed operation are typically single or at most dual articulated for greater stability at high speeds, and are often equipped for multiple unit operation. Pretty much every city in the US which has high speed light rail, including Boston, has followed that model. But when you account for the other side of the physical characteristics spectrum of the system, the relatively slow speeds of the subway and its curvature and clearances, suddenly you find you're in between the two equipment types. Throw in the holdover quirks like on board fare collection via farebox and one man per car staffing, and oh by the way the astronomical ridership that we "enjoy" on the Green Line, and you find that the vehicle that does it all simply cannot be bought off the shelf.
San Francisco has pretty much gone its own way and needn't be constrained by what Boston needs, but I still think Boston and Philadelphia need to do some collaboration. A joint order for Type 9s for both cities sure would bring the unit cost way down, and Philadelphia's Kawasakis, though apparently still solid, are getting very old and are still not accessible.