After 10 years of co-owning a T27 in the NY area all I can say is that it is a great boat. It sails great, looks great, turns heads and the shoal draft is nearly perfect for the LI Sound or Chessy areas. It was built like a Cadillac in it's day but is a much older lady now.
Our T27 has taught me a lot about boat maintenance. This past winter we replaced the entire drive train on our boat with a new SS shaft, hose, Cutless bearing and whatnot. I now know how to debug an Atomic 4 engine and get it running and tuned.
I haven't had to tackle the one soft spot we have on our deck yet. It seems to be a perennial problem with these older boats where hardware was installed and not properly bedded or re-bedded but the decks can get a bit soft. Several T27 owners have undertaken this project (not me) and have photos of their projects on our T27Owners Yahoo group: T27Owners : Tartan 27 Owners Yahoo Group
if you are interested.
A T27 will cost you only marginally less then a T30 to finance yearly but you will likely make up for that with projects you want/need or should do. Once the projects are done it is just a slightly cheaper but prettier boat - I find that the projects are never done though.