The approach with Ross seems to have been more direct so far, as Edes says that the Sox have actively told him they want him back, and that an extension could get done before the season. For Ortiz, all we have no is a general inclination.
The question will be for how much, and how long?
When it comes to Ross, I wouldn't be at all surprised to see him come in at a very reasonable dollar figure and length. While he's been solid for the Red Sox this season, the open market can be a bit of a fickle place, and he may find that it's a harsh judge of his heavy home - road splits. As much of a mess as this season has been, Ross is one of the only thins that really seems to have fit.
The desire for a big payday after a strong year could always lure him into free agency. But, if the Sox don't attempt to low ball him too much, it's not hard to see him inking a very reasonable deal that should help the team weather a short-handed outfield while they wait to get their prospects in line to take over.
Ortiz' situation, on the other hand, is as murky as ever. There's no denying that Big Papi has shown he's all the way back from those two years of uncertainty, but he's still going to be 37, and the slow-healing heel is a reminder of that. With the incredible amounts of cash the Sox freed up, especially headed into a down FA market for 2012-2013, it's almost impossible to see a scenario where they don't offer him a significant amount of money.
The problem there is the years. Ortiz has made it widely known he doesn't want to do the one-year contract thing anymore, but that's really the best scenario for the Red Sox. There are no longer any big contracts to come off the books for Boston until Lackey goes away. The only reprieves they'll find lie in arbitration players, and it's hard to really call it a reprieve to dump Ellsbury's salary (especially since they could end up re-signing him now). What they have to work with for 2013 is largely what they have to work with for 2014 as well. Committing upwards of 20% of that to a 37-year-old DH is a bit of a questionable move.
Still, compared to the alternatives, and the massive contracts we just moved on, it's kind of child's play. For a Red Sox team that's looking to be more disciplined and responsible with their money, it's hard to blink at a couple of short-year deals for a solid outfielder like Ross and the longest tenured member of the team who happens to bring one of the AL's biggest bats with him. Extending both would be a good start towards filling the holes for 2013.