Every trainer is going to tell you something different, I was taught for years to keep my toes pointing forward, so they kind of naturally do it now, but my new trainer HATES it and has me keep them out a bit and im actually able to stretch my leg and calf further down and around the horse. Keeping your toes out at a 40 to 45 degree angle will also keep you much more sercure when your jumping.
If any of you know who George Morris is(the King of Equitation) and Chef D'equipe for the US team.. he also will tell you to ride with your toes out at an angle. You can google any of the big name grand prix rider and look at where they keep there feet.... even over 5 ft jump they have there legs and feet at an angle
You should wrap your ankles! But just remember when your riding "toes, toes toes!" think about it all the time and because of your physical situation turn the whole lower half of your leg in. It wont be as painful and it will be effective! If you think about it every now and then with every ride, slowly your brain will automaticly think it! This is what I have done with my toes and keeping my legs back and on and it WORKED!