As someone that currently works in Boston, I really hope we don't get it. For starters the plan is built around the idea of a 'compact olympics' and building a lot of new infrastructure in and around the city which will most likely cost significantly more than estimated. If you look at the last few olympics, especially Sochi, they all cost a whole lot more than revenue it generated and I feel like our state and local taxes will increase to pay for all of the new buildings. I also don't think Boston can handle in influx of people that would come with the Olympics and travel to and from and inside of Boston will be a disaster.
With that being sad, the two or three weeks when the Olympics are happening would be a blast and an awesome experience (besides the horror of trying to commute to work and get around), but I think the negatives outweigh the positives.