Let me take a pop at this:
1) How can the Red Sox compete in the FA market (without offering those huge contracts), i can't believe that there isn't a huge scarlet letter on this franchise.
Why would there be a scarlett letter on the franchise? Boston is, and remains, one of the most attractive spots for a potential FA. Granted this is largely due to their capacity to spend, but there is certainly no "scarlett letter"
2) some people are touting going out and getting a Josh Hamilton, which i don't understand. Wouldn't that take a contract just like the ones we got rid of? And how would he survive in Boston with the media and pressure? How high risk is he to start his bad ways again?
It's only gonna take one team to give Hamilton what he's looking for so my guess is he will get it but given his history of addiction, two KNOWN relapses, age (32 for next year) and borderline great numbers, I think the offers for his services are gonna be limited. Hamilton is one of the most over-hyped players in baseball. He has a great story, if he stays clean, has very good numbers, but the hype is all around the big HR Derby he had in NY, the four HR game and hot streaks he goes on where he is unconscious. If you look at his entire body of work, he is not an elite player and i think its clear his best years are behind him.
I do not want him in Boston
3) There are no real FA this year - who is avail in 2014
Felix Hernandez will be the prize going into 2014. But there is some talk about an Ellsbury, Lester and prospects deal to bring him to Boston sooner. It's not on the immediate radar but don't be surprised to see these "rumors" heating up this winter.
4) Do we really want to spend the Boras money on Elsbury?
No. And neither do the Red Sox.
5) Could we get Felix? Really the only franchise game changer out there right now (IMO)
See above but you're right, he is the MAN TO GET right now and I can't help but think that a lot of the salary they free'd up today is slated for Felix's pocketbook
As for John Lackey, he is the last of Theo's mistakes. He's gonna get his money, whether he ever throws another pitch in the majors so we all have to deal with it. Hopefully the TJ surgery helps him and he can develop into a #4 starter. No one is gonna take him off our hands, not at that price, and Lackey ain't going anywhere with all that cash on the table so we're gonna have to live with him. Like I said . . . if he can be a solid #4, I think we should be "happy"