Well depends if he wants to try and sub him or if he wants to get back up. I too think he can tie GSP up well from guard and that can be a way he can get it standing anyway. I think he can sub GSP, it will be the strongest wrist control GSP has ever dealt with. He didn't go down to the ground with Shields. It would definatly be the best guard he has been in, especially with ANderson's length.
Sure, he should definatly try to avoid the TD that should be plan A. But like I said, if it comes down to it where he isn't subbing GSP and GSP is just in guard...then I would let GSP get confident by giving up position in order to look for a counter.
ANderson could attack this fight in many ways and has many aspects that he can exploit or challenge. GSP basically has 1 or 2 ways. Wrestling/keeping him there. Or if Anderson gasses from the weight cut he could cruise the 2nd half of the fight.
Tried repping, gotta spread. Im not too sure Silva would sub GSP. I think it would be a lot more difficult for him to sub GSP rather than KO him. I'm not saying its impossible, GSP has some pretty decent sub-defence.
In reference to to your second and third paragraph. I couldn't agree more. Anderson could knock him out from literally anywhere standing, he also is very active off his back. Anderson gassing? Its got to be a viable option. How often do we see The Spider go 5 rounds? Or even 3? Add a weight cut to that it and it becomes even more possible!