1. Yes. I bring a straight razor, brush, strop, soap in wood bowl w/ lid and a cord to hang strop from door knob.
4. All shaving brushes do the same thing regardless of price. I've been using one best badger brush for about 15 years and I think it cost around $40.00. I wouldn't go crazy on your first brush. Try a pure badger or best badger for around $30 - $60.00. An economy boars bristle brush such as a Burma Shave brush for around $5 or $6 would be a good comparison brush so you can feel the difference. Later, if you really want to spend more, go for a silver tip badger.
5. As mentioned above, a $5 brush will do the same thing as a $500 brush. A less expensive boars bristle brush may be more irritating for some skin types, but even a silver tip badger can cause irritation for some, especially when new.
7. I'm assuming you mean honing. I get quite a few shaves between honings, but YMMV. A lot of variables apply here, such as experience and skill. The more experience and skill you develop, the more shaves you'll get before re-honing.
9. To me a shave without aftershave is like toast without butter. Pros - mild disinfecting newly exfoliated skin, astringent effect closing pores, various scents. Cons - additional cost (cold water can have a slight astringent effect).
10. Yes. With experience and skill you will be able to shave any part of your face safely.
12. Personal preference. With propper beard prep you can shave anytime you want.
Good luck,
Scott