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Are you referring to the 1st and last pictures? Because you quoted the entire post.
I don't think the 1st one looks too bad, especially on that blank section of wall. The last one, the entire face of the building looks bad, but it will probably end up blocked by a building on the property in the foreground.
I have a friend who recently sold his place in the South End. He's looking for something of similar size or bigger, with parking, newer construction, and in the city. More and more places in South Boston are on his radar and checking off the boxes for what he's looking for. In my unprofessional opinion, it seems like a lot of the new residential construction in South Boston is tailored to these types of buyers (and renters) - have money to spend, priced out of other neighborhoods, and see a 'value' in the neighborhood.
Just make sure your friend pays close attention to fit, finish, and general quality of the newer construction places to make sure he sees the 'value' there. I had toured a number of brand new units all over west Southie last year mostly just for shits and giggles and was surprised to see how often build quality was lacking. It's probably what happens when everyone is trying to build as fast as possible at the same time and there are only so many qualified builders or actual craftsmen. Things looking good from afar, but woeful up-close was an overall theme.
I hope he finds a good one.