At this point the proposed service has had broad support by local town governments, although more detailed planning is necessary to reflect local input. The primary issue that must be resolved is securing funding to upgrade the tracks so they can accommodate passenger trains at passenger speeds. The upgrade work includes upgrading the tracks and road bed as well as placement and construction of stations. It is likely that most stations will be run by local towns, though some could be operated privately. The railroad has located older surplus locomotives and coaches that could be overhauled and used in the service. Since trains will operate on diesel power on the Housatonic Line and electric power on much of Metro-North they will need to accommodate both systems.  There are few impediments to completing the track upgrades except funding.

As of 2019, MassDOT has begun a $21 million overhaul of the Housatonic Line, consisting of replacing ties and rails along the 37-mile stretch of the line in Massachusetts. This is a huge step in the right direction for restoring passenger service, but repairs conducted in Massachusetts are of limited use if funding is not secured for similar upgrades to the remainder of the line in Connecticut. Therefore, securing funding for track and other infrastructure upgrades in Connecticut is extremely important for restoring service, and remains a major obstacle to doing so.