In this game: http://www.wargear.net/games/player/65531

Is this a legitimate strategy?  capn is blocking me from taking the staging area (due to D1VD1 dice) so I can only take squares for the rest of the match?

This is different from the game description which states there should be a D1VD0 at the staging area.

~ATH

I really goofed when I made the scenarios and did not properly implement a number of the twists that the final board had put in.  The D1vD1 error was fixed on Monday, so the strategy that your opponent is using is not possible in new games.  

Don't know what to tell you about that game, other then he should play it straight and get out of that territory, or terminate the game.

Octagons Starting Strategy:

So as first player in Large Start Squares (LSS), what is the best strategy for determining the opening tile placement?  Many times I've heard the pros say they are connected on one side or the other but is that really true?  Doesn't the second player even have a chance to break up that movement?

It's all semantics here. But, when I say "I'm connected to the left side", I do mean that there is NOTHING my opponent can do to stop the connection. Furthermore, I mean that the play connecting to the left is, as far as I can tell, independent of all other play.

As first player, I look for spots connected to both sides. It's so complicated to work it out from move one, but I still  try to work out as much as I can. Sometimes I can see the connection to one side, but the other side is too complicated to work out. Nonetheless, it "looks connected". Those are the spots to look for. Sometimes the second player is winning, and I instead settle for the "best looking swindle".

I don't have a great method outside of calculation because the random setup makes each situation so different (which is why we like that scenario A LOT). However, my "calculations" are informed by "shapes" (jumps, standard sacrifices, etc, that I've worked out before).

Short Answer: Hugh is smart and being smart is the best strategy.