It seems that with a bit of patience everything works out fine except for the 2 armor skills. (And those don't even have master trainers accessible under my self-imposed limtations - what was Bethesda thinking? I ought to get my money back.)
The trouble is that my conditions don't allow for the easy power-levelling - no good potions (so no ungodly health regen), no good enchantments (so no free restoration), and really low armor values.
The current plan is to just create a crazy big pile of restore health potions to complement the equipment (fortify health so my character can survive stronger attacks) as well as fortify health potions but I'd really like to use an easier approach. Any ideas?