If/when the Raiders leave Oakland, I think that would allow them to renovate that stadium more.
I think Montreal is still a longshot, but last weekend was certainly positive and I'd say their chances are much better than before. Of course, finding that owner with deep pockets who is willing to do what it takes to build a winner there will be an adventure in itself. I do have my doubts if they could be successful over the longterm though. It was one weekend after all and a decade after they last had a team.
I saw some talk about expansion last week -- which isn't likely going to happen -- if anything, they need contraction, which the Union won't likely agree to. There's just not really anymore viable markets left like you said. DC was the last one and that was only used used done after baseball had exhausted it's options. Playing at Olympic even only over 1-2 seasons could pose a challenge, they aren't allowed to hold events when enough snow is expected, not sure how that would apply to other bad weather.
I guess they could tear down Mt. Davis, which would improve the aesthetics, but since that part never gets used for baseball as it is, I don't think that helps the A's revenues at all. And since the current site sits below sea level, I think water is always going to be an issue there (though I'm sure there's more to their plumbing problems than just that). Pouring millions into that stadium just seems like throwing good money after bad.
I think Montreal baseball fans get a bit of a bad rap. Under the circumstances (horrible stadium, horrible ownership, best season ever ended by a strike) it's not hard to understand why they stopped supporting the Expos. In some ways I think it mirrors Baltimore with the NFL. People pointed to how the Colts had lousy attendance in their final seasons, without really seeing the underlying causes. And once Baltimore got another chance, with good ownership committed to winning and a good stadium, it's worked out great. But like you said, finding that ownership, and building that stadium would be a challenge....but if it were to happen, I think Montreal could work.
But in the meantime, MLB seems to be willing to just let the A's sit there operate as a small-market franchise in what is easily the 2nd worst stadium in baseball. And I don't know how much I buy into Kawakami's statement about the other owners being miffed over the A's profiting off of revenue-sharing. If the owners don't like it, there's two things they could do: 1) change the formula in the next CBA so the A's don't get as much money, or 2) stop blocking them from a solution that could possibly get them off revenue-sharing.