As someone who has never bought a paid F ticket in his life...under a grand for revenue F from BOS to anywhere warm over Christmas/NY sounds like a relative steal.
And $200 for an RT guaranteed* upgrade sounds like beyond a no-brainer.
Heck even if I was an EXP I'd probably buy the F ticket.
*With the caveat that this is probably one of those weirdo fake F fares and in the case of IRROPs you'll possibly be flying Y.