I have tried all 3 models and have settled on the Roclite 295 as my preferred hiking shoe. The 330s and 295s seem to be virtually identical in fit but have a different "feel" on my feet. The 295s feel more flexible while the soles of the 330s have a stiffer, more "plate-like" feel. This may be due to the use of softer rubber and a different shank design on the 295s. The 330s have slightly thicker padding around the ankles. In general, the 330s feel a little more comfortable when I put them on but the 295s feel more comfortable when I'm walking.
I don't like the 305s as much as the 295s and 330s as they are narrower in the toes.
Frankly, I think the differences in midsole cushioning are slight between the various models and are outweiged by other factors such as flexibility and type of rubber on the sole.
The 295s supposedly have more cushioning than the 330s but the softer, more flexible sole also means you feel the rocks underfoot a little more.
I have used the 295s extensively in the Sierra, on and off trail, and they have worked well for me. However, I only get about 200 miles out of a pair. By then the sole lugs are generally becoming worn and the soles starting to separate where the foot bends. Also, the webbing loops are a weak point and need to be improved. One or more loops have broken on every pair I've had. When that happens I use a different lacing pattern or poke a hole through the upper next to the broken loop.