a few things regarding fit and deep drops:
All else constant, it is more comfortable to ride low drops if you are:
flexible
lanky
young

Deep drops may make your neck/back hurt if you ride them more than a few hours in the city.

For city riding you will probably not spend much time in the drops if your bars are that low, so you might as well put the padding on the flats.

Most track rides who ride bikes set up as above do so for a couple of minutes at a time on a perfectly smoothe surface with no cross traffic.