Hey Jason,
Typically all boats will favor one side or the other. On some that favor is significant. MOST boats will favor the port side, but I would recommend you play with both sides. ALSO, something I think that is more important is which side you ride front side on. If your stance is Goofy then you'll want to weight the "dark side"
otherwise you'll weight the regular side.
I don't believe that there is an unsafe side.
There are a number of good boards that will fit you. Trick Boardz, Shred Stixx, XBC, Inland Surfer all have boards for bigger guys. All of those manufacturers are pretty helpful in sizing a board for folks. Personally, I like to chat with the manufacturers and get their input. I'd recommend checking each of the offerings from those folks.
Inland has the Red Tide
Shred Stixx has the BlowFish
Trick Board has the Mojo (in various sizes)
and XBC has their Longboard in a chubby
I think those would be a great place to start.
I think that a wakesurf specific rope is wise. I know most folks don't use one, but to me the safety issue makes this a no-brainer. We personally prefer the T-handle that John Boy Holmes recommended. I got mine from Shoreline Lakeboards but they no longer carry it. I saw that Liquid Force makes a similar T-handle rope.
Good luck and keep us all posted on your progress.