You need to start a log/diary of exactly who what and when on everthing. The city has a program to cover all things like this, and it has to be readily available to people. Boston is self insured no doubt, but there is a program/division just to handle stuff like this.
Start sending certified letters with signature of receipt with your claim and request for contact to the following, Transit/Transportation Office, Public Works Dept., Police Department, Mayors Office. I would also do the email thing, but mainly for possible response and tracking of their response. This will get you locked in on your time of claim.
Then it's just a matter of leg work and documenting every minute/cost you put into getting this rectified. If you get the run around is where the time/cost involved comes in huge for you. They won't be forced to compensate your for a little time, but if this drags out and you are getting the run around they are liable for all your costs including interest. For a couple hundred...probably not worth it....for 2500 its darn well worth it.