I've nothing to cite for this, but I'd say the following:
When should you bore a block during a rebuild?
Only if necessary - if the bores are damaged, scored or heavily pitted.
How do you determine if the block should be bored?
Check the bores - if one or more are damaged, scored or heavily pitted, then it will need boring. light scratches and surface rust can be dealt with by honing, without the need for a full rebore.
How do you determine if the block can be bored?
Measure it! Most engines will have a limit as to how much they can be bored - typically something like +40 thou (thousandths of an inch). It helps if you know the history - has the block been rebored before? If you bore it too far, the cylinder walls will become too thin. If it has been bored to the limit, it might be possible to sleeve it. You may also be restricted by piston availability - off-the-shelf pistons usually only come in a few sizes, typically +10, +20, +30 and +40 thou.
How do you deal with sleeved blocks?
Measure the thickness of the sleeve - again, there will be a limit as to how much they can then be bored before the sleeve becomes too thin (I'm not sure if sleeves can be removed and replaced with new, I'd assume they can...)
Any pitfalls or things you should look out for?
Wet-lined engines - common in aluminium-block engines, these are effectively already sleeved, with an oil jacket on the outside of the sleeve, but often the liners themselves can be replaced, in the same way as re-sleeving a normal block. Beware when dismantling a wetlined engine, as the liners can often stick to the head and become dislodged, requiring them to be properly reseated before reassembly...