re: toe clip problem
from your photos it looks like you are using pedals with no "bite" (virtually no serrated edge) and a hard rubber clip with a smooth bottom, neither of which offer much friction to prevent your shoes from slipping out....you could try lowering the rubber clip relative to the pedal platform so your shoe can engage the edge of the pedal for more "bite"...if that doesn't work I would recommend switching to a "rat trap" style pedal (see Harris Cyclery pedal page) and good quality (i.e. not Nashbar) metal clips rather than rubber clips which twist and deform under minimal pressure and provide virtually no gripping force.