Re: Congress St Garage is being sold.
While I wouldn't want a lot of them, I don't find the garage to be that detrimental to the pedestrian experience of Congress Street. Losing the view corridor is unforgiveable, but otherwise I don't have much to complain about.
Back on the topic of how to arrange the site, the eastern half of the property -- where the bus station is -- is by far the smaller of the two plots, which would make a good spot for a hotel or residential tower; for this exercise I'll go with the hotel. It would need a big base for conference facilities, so let's say you put retail on the first floor or two, occupying the same sliver of land that the current ground floor does, have conference rooms cantilevering out over the bus stop on floors three through five, and put a 20-story tower on top of that, making for a building no more than 300 feet tall.
Then on the west side, put up a large office building of around 50 stories on the southern portion, where it's furthest away from the Triangle and North End, and in the west-northwest corner put up a residential tower, 30-40 stories tall. Both towers would sit on a retail podium of 3-5 stories.
It should look something like this. As seen, the office building would have 36k sq ft floorplates, and at 45 stories would yield 1.6m sq ft of rentable area. The hotel, at 20 stories, would contain around 625 rooms.