The way I like to think about the dimensionality of a quantity is that it is characterizes how the numerical value of the quantity changes when we make use of our freedom to arbitrarily scale units.
Since all the SI units like metre, second, and so forth are defined completely arbitrarily [e.g. 1 metre is the distance traveled by light in 1/(299792458) of a second -- there's clearly nothing special about this number], we don't expect the form of any of our equations to change if we instead measure length in half-metres, time in minutes, and so forth. So suppose we change our units so that the numerical value of lengths are multiplied by some factor L, whereas numerical value of times are scaled by another factor T. Then since velocity = (distance)/(time), the numerical value of velocity is scaled by a factor LT-1, so this is the dimensionality of velocity. The requirement for "dimensional correctness" (i.e. the two sides of a physically meaningful equation must have the same dimension) then follows from the fact that, for the equation to still be valid when we rescale our units, the two sides of the equation have to transform in the same way.
When you think about it this way, a dimensionless quantity is one whose numerical value doesn't change when you scale your arbitrary units. The reason we think of an angle measured in radians as being dimensionless, is that, unlike metres and seconds, radians are not an arbitrarily defined unit. They are a very special unit of angle which are chosen to make our equations as simple as possible (for example, (d/dx)sin(x) = cos(x) if we measure angles in radians, but not otherwise). We can't change units of angle and expect our equations to retain the same form, so an angle measured in radians is dimensionless (of course, we can say the same kind of thing about a solid angle measured in steradians). On the other hand, degrees are a completely arbitrary unit of angle, so if we measure angles in degrees then we should no longer think of them as dimensionless.
If we wanted to, we could also decide to measure quantities such as time and distance in http://en.wikipedia.org/wiki/Planck_units" , so that c = hbar = G = 1. As these are "natural", not arbitrary units (as reflected in the fact that formulas take simpler forms in these units, since lots of physical constants are just equal to 1), distances and times would then become dimensionless as well.
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A question for those advocating Siano's "orientational analysis": is it possible to derive the rules of orientational analysis from some symmetry of physical laws in the same as way as I did above for ordinary dimensional analysis? Presumably from rotational symmetry? Siano seems to suggest this is possible in his papers, but I can't see where he actually does it. Also, that would imply that orientational analysis is no longer valid in problems with a preferred direction, due to, e.g., the Earth's gravitational field.