at first I read this and thought, "What's the guy in Kansas worried about hills for- what kinds of hills is he talking about?"

then I did the math:

1/4 mile = 1,320'

an elevation gain of 300' in 1/4 mile = 22.72% grade!

Do you mean an overall gain in altitude of 300' on your commute with gradual hills (5% or less- meaning in a 1/4 mile you might gain 60' in alt.)? So in about 10 miles you might have 5 long hills or so but not too steep?

Some of us take our hill climbing very seriously

I have a feeling your hilly route is the best route and it sounds like more fun- and isn't that what it's all about- and doing those 22% hill climbs will prep you nicely for the annual Mt. Washington Hill Climb or to be King of the Mountains in the Tour de France.