Hello,
To answer your questions:
1) If you want to apply this year and are ready to, it might make sense this year (caveat--see answer 4 below). If you don't get in, for most schools, there is no downside to being a reapplicant as long as you can show growth in the interim. If you either decide not to apply this year or apply and don’t get in, I suggest focusing first on further developing a strong track record at work of leadership, impact, and achievement. The adcoms to all top programs want to see growth and advancement in your work experience. Second, further research
your goals to make as strong a case as possible for them.
2) Among the schools you mentioned, Kellogg would be a high but reasonable reach; the others would be on the border of on-par and reasonable reach. You might consider also Darden, which is rich in marketing related concentrations and perspectives.
3) I suggest you choose the area you’re most interested in and focus on that for your post-MBA goal. That’s the appropriate way to approach it, not which way is easiest.
4) This too you will have to decide. It’s a personal and a career decision, not an admissions decision. (Though the fact that you’re asking these questions makes me think that you should wait to apply till you have worked these things out.)
5) R2 and R1 are roughly the same. It’s R3 to avoid, if you can.