Just in case I haven't already riled up enough sports fans reading this thread, this would be an excellent location for New Fenway Park once the city and the Red Sox are forced to confront the harsh reality that - structural integrity be damned - Fenway Park can't survive another 47 years of active use and placing it on the Register of Historic Places has likely precluded any sort of significant further renovations or upgrades. It's time to pull out of Fenway, and preserve what we can of it as a museum.
Being on the National Register does not in any way preclude necessary renovations to keep a structure in use,
especially if that use is the same as what it was designed for. The HP standards are not designed to create museums. In fact, a great deal of the community now believes that museums are just about the worst use for a historic structure, since it is typically unsustainable from a financial standpoint, and also insensitive to the buildings genesis: as a working, functioning, occupied space.
The National Register, and the Standards for Historic Preservation that govern how to work with registered properties, are a guide on how to work with them as to not undertake work that would undermine their cohesiveness. It is not meant to place an undue burden on the owner (or steward would be a better term), but ensure that what makes them special in the first place is not destroyed.
A good example is one of Frank Lloyd Wrights houses, where the cantilevered roof had a design flaw and kept bowing every few years. They were able to replace the entire structure with steel, but simply had to make sure that from the exterior the changes were not evident, and that they well documented the work and left indications of what was there prior. That's pretty common: iron or wood being replaced with steel, concrete reinforcement hidden inside a brick wall, etc. Additions are also perfectly acceptable, they just have to be
visually distinct and identifiable as a later addition, removable with minimal work, and do as little damage to the original structure as possible. As much as it's hated, the Johnson wing of the BPL is actually a pretty good example of this. You could tear it down and the original structure would be pretty much still there.
On top of not being as much of a hindrance is typically perceived, preservation work that sticks to the standards can get 20% of hard costs back from the state, as well as 20% from the feds in the form of tax credits. So the extra costs associated with the complications in dealing with these properties are mitigated, as long as the work is done correctly. A properly done project can sometimes even be cheaper than building new, and it is by far more sustainable. The notion of a building having a "lifespan" is also new-age BS coined to allow buildings to be built cheap and fast, expecting them to be torn down instead of maintained. Fenway is older than this belief, built to be rehabbed and modified indefinitely, much like the housing stock of the adjacent neighborhood.
The issue is, 99% of architects and contractors have no idea what to do with historic properties. They look at a project and the first instinct is a gut and remodel. Cover it with glass, modernize everything. Make it "better". When they are told they can't
it just becomes impossible! Part of it is ego, part of it is lack of knowledge. Many projects don't use tax credits because they don't understand the process, think it won't work for what they are trying to do, or a million other reasons that really boil down to not hiring a good preservation consultant.
Landmarking properties, and by extension the HP standards are guidelines, like building codes. They restrict what you can and can not do for an established greater good, not to straight up block anything from happening. Hardly anything is impossible to do with a registered property, it just takes setting aside personal preference and ego, a healthy dose of cleverness and innovation, and working within the context of the existing building. It always amazes me how working with old buildings is regarded, as if it is some undue burden that must be aggressively dealt with, like mold. Designers are inherently problem solvers: turning site constraints, budget, program and codes into a serviceable (and hopefully aesthetically pleasing) building. I for one love working with the challenges inherent in this work, but to many it seems like the bane of their existence.
Looking at the progression of HP, it's really very similar to how we see urban planning. First they thought it best to tear everything down and start with a clean slate; now it's seen as better to work with, and expand upon the bones of what's already there. Fenway is a serviceable structure, and I think there are several ways they could squeeze more life and amenities out of it.
If it were me, I'd use 1960 as my starting point; after the field dimensions were basically established, light towers, green monster and the organ installed, but before the majority of the roof and upper deck seating was added. From that period, I'd start with a brand new second and third level, extending over the Jeano Building and possibly cantilevering over some of Van Ness. You could get a ton more seating out of that park if you tore off everything above the roof, instead of supplementing the mess that has been cobbled together over the past 50 years. Just about the only thing you couldn't do would be to remove the obstructed view seating. Its technically possible, but it's such a unique and well known part of the park they would have to stay.
For something more dramatic, I'd look at demolishing the Cask 'n Flagon and the garage next door, and reorienting Landsdowne to meet Brookline Ave at a 90° angle over the pike. Use all that space for new retail, amenities, and an expanded third deck in place of the monster seats. You couldn't mess with the facade of the Jeano building , but a triangle-shaped parklet could be created where Lansdowne was for a new entrance gate, with some seating cantilevered above.
The big issue is a project to really bring the current Fenway up to spec by tearing down everything post 1960 would either have to see the Sox play somewhere else for a season, or have a few years with drastically reduced seating while the renovations were underway. There is no way you could pull off something of this magnitude during the winter break.
If the sox were to move, I for one believe they would loose a lot of what makes them who they are. The brick and mortar Fenway Park is just as much a part of the team as the logo. To quote the NPS's page on the park:
Fenway Park has acquired significance beyond its role as the place where the Boston Red Sox play baseball. It is tied to a symbiosis in the relationship between the team and Red Sox fans and an entire region, and Fenway Park has become a place of pilgrimage, a place to experience even when there is no baseball game underway. The crowds of more than 200,000 visitors that tour the ballpark each year do not take into account those who, when the ballpark is closed, walk by, come in tour buses or by car, get out, take pictures of the park, or take their own photo at Fenway Park.
The nature of the experience of Fenway Park derives from the intimacy of the space and the proximity of the fans to the team (as well as to each other,) and from the pleasure of being a part of the continuum in the team's history as well as the past longstanding agony of enduring the team's failures. All are participants in whatever transpires at Fenway. The tradition of attending Red Sox games at Fenway Park (and perhaps the actual tickets to the seats) is passed down through multiple generations, and the shared experience of children attending with their parents or grandparents creates a cherished memory.
That's something you don't get if Fenway is made into a museum while the Sox play in some replica stadium with no tie to why the field is the way it is. You don't get Kenmore Square, the Citgo Sign, Yawkey Way, or every other little quirk that makes seeing a game at Fenway so much more unique than most other ballparks, or hell, sports venues in general.