Oh, thought about one more detail worth considering -- especially if you're looking at the Whaler -- weather. Specifically rain and/or cold.

The center console/open bow boats are absoultely amazing on nice days, there's no question. But on a rainy/cold day, the closed bow + canvas on a cuddy is a big advantage when you're moving around, or even just trolling.

Ditto what Summerun said about motors -- IMHO a Yamaha or Honda 4-stroke is what you want. For both the main and kicker. This gets you out of mix-in oil, better fuel economy and a completely unified fuel system (e.g. a single big tank).

The points here about compromise are of course correct -- good luck in your search!