Circuit - you really need to get some text books and start studying. The questions you are asking are pretty involved for a quick answer to be completely correct.
That being said, I'll take a shot at some short answers. Please realize that there is much more to the subject than I will attempt to answer here.
The 'islands' on your planes are called splits. You are using split planes. Whenever a high frequency signal path passes over a split in a plane, there is a change in impedance. That change in impedance is a function of the width of the split, the frequecy components of the signal edge (for digital signals), and the availability of an alternate path. Such impedance discontinuities cause signal distortion. The alternate return path, when the plane is discontinuous, can be through bypass capacitors, or around and/or through other components. You should have the power supplies well bypassed at each critical IC, so the most likely route will be through the nearest bypass capacitors. In general, it is best to avoid routing over splits in the first place.
Differential signals do not rely upon the underlying plane for signal return. However, the impedance of each side of the line is determined by the proximity of adjacent planes, as well as the spacing between the two sides of the differential pair. You should try to avoid making a transition from top to bottom with sensitive differential pairs - again, realize that low frequency, low rise time, signals will not be affected to any measurable extent. The concern is with fast edges, or high frequency RF.
There are many software tools available for analyzing crosstalk. A good one that is easy to use (but moderately pricey) is Hyperlynx from Mentor. A simple, much less accurate tool, is free from:
http://www.ultracad.com/ct_calc.htm
An expensive, but sophisticated and accurate tool is:
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As you suspect, board level simulation needs something like PSPICE, or SPICE. Each component needs to have a model appropriate for the frequecies in use.
Do a little searching on Google. There is a lot out there to help you get more information on all of the above. An excellent place to start is:
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