Advantages - the only substitute for cubic inches is rectangular dollars. Boring does several things. First, more cubic inches means more air fuel mixture, means more chemical energy available to convert to sensible energy. Second, assuming the heads are not changed and the piston deck height and valve notch/dome/dish volume are not changed, a larger "cylinder" gives a higher compression ratio for a given set of heads. Third, a larger bore unshrouds the valves slightly, giving better flow efficiency.
Disadvantages - beside the obvious, i.e. the cost for the pistons, boring, re-balancing. If the remaining cylinder wall is "too" thin, you can have overheating problems and ring sealing problems.
There is no "advantage", the only logical reason for boring a 350 sixty over is to get a good clean round cylinder if a smaller overbore won't accomplish it. There is not enough increase in displacement to have a perceptable effect on power in most applications. The less overbore needed the better, especially if you plan to keep the engine for a long time. You may need to rebuild it again someday and on most 350's .060" is about the limit. If you need more displacement stroke it or start with a bigger engine to begin with.
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