All well-taken.
A little further investigation just now revealed that it's suspected that Dean may be back, but yes, I'd forgotten that he'd been put on IR.
They just moved up a practice squad LB on Monday, so you're right, there's some decent potential for Leonard to get some PT if signed.
1. Okay. Maybe that's important to him. But I think that would be more of a tiebreaking factor. There seems to be a lot of teams in both conferences this season that can make an argument that they're a SB contender. As long as one of those is among the higher bidders for his services, conventional wisdom would be that he'd go for that one, whoever it is.
OverTheCap.com has DAL with about $6.6m of cap space, PHI with half that. That could be important.
2. Two thoughts. From Leonard's perspective, I don't see "depth at the position" as anything of merit. He doesn't want to go somewhere that he merely represents depth if he can help it. From the Eagles' perspective, though, maybe it would be attractive to insert Leonard as a stop-gap for Dean's absence, and anticipating that if Dean returns, Leonard still may have performed too well to re-insert Dean into the starting line-up.
3. Relationships? Pardon my repeating myself, but what I said was that the relationship with a player in the huddle with him and in the film room with is inherently going to have had more time to gel... than the relationship with a coach on the other side of the ball who he's only been around fairly tangentially. And thus, the capacity for Gilmore to influence Leonard would be superior. Leonard hasn't played for Sirianni, so it's not even as-if he'd be naturally more familiar with Sirianni's defense. And, add to that, who doesn't want to play for Dan Quinn... he has guru status in the league at this point.