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There is still surface lots across the street and available space in the Assembly area. I don't think they'll start demolishing parts of the garage any time soon. Maybe we can start talking about that after the strip mall, 5 middlesex, the additional couple of parcels, and even the Circuit City/Home Depot area is built up. But that's not the foreseeable future that's far in the future. I feel like we'll have self driving cars by that time eliminating the need for parking in urban centers.
I didn't just say to do the garage retro-fit, I also showed the part of the street where theres still room in front of the garage to build. No reason why they couldn't build something there now to make the street a little bit more ped friendly, like they did already on Foley st.
https://postimages.org/
You could make half of the street pretty good for the time being then later on do the garage retro fit. I think this is more pressing than some of the far away parcels seeing that this is right in the core and it affects the downtown area a lot.