For street riding it doesnt matter a lot.

Being fairly strong, and knowing your way around will make up more time than any wheels you toss on.

I like a light shallow rim for all around, since youre stopping and going so much. I run some volos with 20/24 spokes and ive had them trued once, and on the rear that was due to some hellacious circumstances of a chain falling and catching and bending a spoke. So I dont buy that shallow rims cant be 'bomb proof'. Granted I keep the rubber on the ground, but I do ride this on very long rides. I do think this trend of really deep rims like the b43 pretty funny on wheels that very well may never see the track. And aerojokes just make me laugh period.

If I had $300 bones and needed a some good wheels I would probably buy some aeroheads, lace them to some dura ace low flange with some basic double butted spokes. Not the best winter wheels, not the coolest, but theyd be smooth and light. If you wanted to save a couple bones and have something better for the winter with sealed bearing maybe the miches.
Or if you want something flashy, dont buy an aerojoke, get a trispoke or something thats at least aero.