1) Yes you may carry medication, BUT only if you have a prescription for it. If you have no prescription, I'd advise you don't. You run a risk of being charged with drug trafficking.
2) Yes, indicate approximate prices. The values don't have to be the actual amounts you paid for the items.
3) All the luggage you have on you should be listed on the goods accompanying list. Simply state the number of bags and assign an approximate value for the clothes e.g 4 bags of clothes - $300.
4) No it's just one list for the entire household, but should be under the PA's name, ideally.
5) Yes, take a picture for each piece of jewelry and print it. Be sure to attach the pictures to the corresponding list - to-follow or accompanying.
Lastly, make 2 copies of each list. The CO will stamp both copies; retain one copy of each (B4 and B4A), the other copy will be for you to keep - you'll need it to clear your items when they arrive.
All the best.