Massachusetts is one of the few states that are actually losing population year in and year out. In order for the bonds to pay for themselves the resulting development would have to attract new jobs to the state and not just move in-state office space closer to Boston. Methinks this a bond issue even Beacon Hill can't pass with a straight face.
Unlike Philadelphia, Boston does not have a city wage tax (an extra tax levied on employee wages earned inside the city limits). This is a good thing for Boston, I saw first hand how the company my father worked for (in Philly) made employees happy by opening offices in th suburbs. Everyone got a 2% raise and had a shorter commute! Menino doesn't have to cope with that kind of harm, he just has to cope with state flight mostly of the northerly kind (NH).