I don't see rule 5 being an issue this year. I think our bottom of the 40 man roster has some guys we can do without- like maybe Brentz, Elias, Abad & Holaday who have zero options.
We (may) lose Papi, Ziegler, Uehara, Tazawa, Hill & Hanigan, but we have added these guys from our 60 man DL: Worman, Sandoval, Swihart. I think we're at 38 now. We can afford to get down to 34 or 35 by trading or DFA'ing some or all of the 4 I listed. There's also Marrero (1 option) and Jerez (2 options) that are not high need players.
I don't see a lot of players that other teams would want on their 25 man roster all year, but here's the list soxprospects.com has:
The following players will be eligible for the December 2016 Rule 5 Draft if they are not added to the 40-man roster by November 20, 2016:
Danny Bethea, Ty Buttrey, Jamie Callahan, Carlos Coste, Ryan Court, Allen Craig, Jake Drehoff, Jeff Driskel, Jeffry Fernandez, Pat Goetze, Reed Gragnani, Taylor Grover, Justin Haley, Juan Hernandez, Dedgar Jimenez, Raiwinson Lameda, Anyelo LeClerc, Tzu-Wei Lin, Deiner Lopez, Austin Maddox, Kyle Martin, Mike McCarthy, Daniel McGrath, Simon Mercedes, Mike Meyers, Mike Miller, Yankory Pimentel, Tim Roberson, Javier Rodriguez, Jake Romanski, Dioscar Romero, Ramses Rosario, Jose Sermo, Teddy Stankiewicz, Aneury Tavarez, German Taveras, JT Watkins, Jordan Weems, Jantzen Witte, Luis Ysla
I don't see a big problem at the bottom of our roster, even if we sign 4 free agents.