There are different opinions regarding this. So having done both I'll add mine. The yard likes them down for a couple of reasons. First of which is they can charge you for taking it down and putting it up. Secondly, the mast up creates windage that given the correct circumstances could topple the boat and damage nearby boats. So they charge you extra for more poppet's. Also being in NE you get Ice. So if you don't cover the boat you may get damage from falling ice from the
rigging.
Ok now the pluses, It's less money for you. You don't have to fully re-tune the
rig in the spring. Your mast and boat won't get beat up during the process.
A simple compromise I use is every other year, using the down year for inspections and repairs. With a 27 footer I won't hesitate to leave the mast up.