1) While I am opposed to bringing Kimbrel back for the rumored years, I do think re-signing him is on DD's radar. I like the idea of signing oft-injured Garret Richards as a closer with the hopes that the lesser workload works in his favor. But I think DD will stick to the experienced closer market and if he doesn' bring back Kimbrel, he will try to land someone like Jeurys Familia, Britton, AJ Ramos, Cody Allen, or Kelvin Herrera. The closer market actually has enough options that I doubt DD gets creative.
2) I'm sure Eovaldi is on is radar. He did trade for him, after all. So it will come down to what the demands are.
3) If the Sox do pursue a 2B despite having some depth (Quiroz, Hernandez, Holt, Nunez), maybe someone like Logan Forsythe? I have heard rumors about DJ LaMahieu as a good fit, whcih he is. But that depends as he is an excessive get if Pedroia is actually healthy. At 1B, the Sox might pursue Matt Adams or bring back Pearce. I doubt they go even heavy enough to acquire Justin Smoak, since they do appear to like Moreland. Siging Marwin Gonzalez would give them both 1B and 2B, among other positions. However, unless the Sox deal a few MLB players, there might be issues squeezing these players along with Swihart, Holt, Nunez and Leon on to a 4 man bench. I do think Swihart is trade bait.
4) I wish they tried that this year.
5) Mostly because he is the best defensive RF in the game today. It's not broken. Don't fix it.
6) The Sox will certainly try farm system relievers. They do every year. But probably not on opening day, unless the pitcher is out of options.