1) I think you could do an abbreviated SS (2-3 weeks), followed by a decent run on advanced novice.
2) I normally don't do calorie tracking, but here's what I'm thinking 275 pro/ 275 carb/ 75 g fat and on Monday and Friday go 230/400/65.
3) Do one on your last day of training of the week.
4) Stick to single ingredient foods for all your macros. More specific stuff on what exactly to eat gets into consult territory but this should be a good start.