It's always a good idea to at least have a plan, especially if you are going to be drilling holes in your house and cutting into your walls.
Now, to develop this plan, you need to have an idea how your home was build.
Go up into your attic and take a look around, figure out where you can get to without killing yourself and where wireless would probably be a better idea.
Okay, the way this is going to work is that all of the cables are going to go from where you want them to some central point in a hub-n-spoke manner.
Negotiate with your wife on giving you a shelf in that closet in the middle of everything. The closer this closet is to where you want your jacks to be,
the shorter your cable runs need to be. Remember that all of you runs will terminate here so try not to pick a place that is terribly difficult to access.
For the drops, it's a good idea to avoid exterior walls (they usually will have a bunch on insulation and possibly some extra 2x4's running through them
horizontally). If you see an exterior wall with a power line running down it and are thinking about just following it down, don't.
It will kill your network performance.
One more thing, run more cables than you need. It is just as hard (and only slightly more expensive) to run 4 cables to a 4 port wall plate than 1 cable
to a 1 port plate.