Swapping brake pads is about a 5 minute job. Hard to imagine too many situations where you wouldn't have time to do that.

As a road racer from a windy state i always suggest the shallower wheel, just not worth the pain fighting the wind. TT bike can handle a slightly deeper wheel due to the weight distribution, but on a road bike for all conditions i say 50mm or less (150lbs). I can ride 60-70mm 80% of the time, but that other 20% is quite difficult. The Zipp 303/404 or specialized CLX 64 have the best brake tracks, Enve is good but overpriced. Unless you are road racing get clinchers, tubies are not worth the work for anything other than crits (ride the flat to the wheel pit, low pressure, no worries of pinch flats, etc).

HED Stingers are great wheels, brake track is not as good as the two mentioned above. The big advantage is price, i have seen stingers for 1400 a set brand new online (check the classifieds here for a few online shops). Their hubs are also really good (own a set right now).

Anyways, at your price range the Specialized/Enve are no go, and honestly that is a good thing. Unless you are road racing, get the 303, if you are road racing i would get the stinger 60.