I'm going to play devil's advocate here.....From Hammond's side of things, not being a "team player" and forcing the Sens to either deal him or put him on waivers could end up paying off as a smart choice if he is claimed. Had he agreed to go on a conditioning stint, the Sens would have been able to buy time, and ultimately he'd be stuck in a 3 goalie carousel.
If he's a realistic guy, it is pretty obvious that his time in Ottawa might be up with Condon coming in and playing well so far, so forcing a change of scenery sooner rather than later would be beneficial.
There are only 30 backup jobs in the entire league, and there are probably more than 30 goalies in the world who can do an adequate job of being an NHL backup goalie. Getting one of those spots is a lot of the time about being in the right place at the right time, and keeping your foot in the door once it is in there. Let's say he accepts the conditioning stint, a lot of the teams needing goalies right now likely move on from their situations, he toils around as Ottawa's third goalie for the rest of the year, gets bought out and loses 400k that he'll never get back, and then is out of the league for good. He forces waivers, if someone picks him up who needs a short term solution, he gets a chance to play in a fresh situation and possibly improve his situation the same way that Condon did when he came in and stole Hammond's job.
Would I be happy as a Sens fan if we lose Hammond for almost nothing to waivers (Don't the Sens get 50k in cash if he gets claimed lolmelnyk?) rather than dealing him for a pick? No. But I can understand in his situation why he would play things this way.
Although, it could just be that he is a lazy guy who doesn't want to ride the busses anymore, understands he lucked into getting 4 million dollars to retire on, and is just trying to coast his way through the rest of his contract knowing he isn't good enough to be a starter. WHO KNOWS.