Firstly, congratulations on your admissions to CBS - that is an incredible achievement. And congrats on the promotion, too -- all in all a pretty good year for you so far!
I totally understand your conundrum - Haas is my alma mater and given your specific interest in technology and west coast companies, I can understand why you want to go there. This is a really tough choice! Haas has definitely gotten more competitive over the years - with such a small class size (240 students) and a flood of applicants, Haas consistently has one of the lowest acceptance rates among the top 10. I don't know that there are any meaningful stats around reapplicants -- there is a great deal of variability in reapplicants' applications, (those who've not improved their profile vs those who really have), so it is very tough to say. It just depends on how much you improve and how well you articulate your improvements.
I can't really give you an answer on your problem, as it's a very personal decision, but I can maybe help you think through it a bit more.
Obviously there is the risk that you reapply to Haas and don't get in. So, if you do choose this route, you should really understand what your back up options would be. One option would be to apply to other west coast schools at the same time, so that in the worst case scenario, you are at UCLA or USC and still in very close proximity to Silicon Valley and all the tech companies. Or you could stay at your company and start moving towards the strategy side of things -- perhaps it would take a little longer to make that transition, but it's an option. You could also apply to part time programs and do both at the same time. Since you want to stay in the same sector, the full time MBA may not be the only route for you. Does the promotion help you towards that ultimate goal? If so, maybe it makes sense to take advantage of it.
If you start J term at Chicago, you'll come out with a very strong strategy and business skill set. Chicago is a top school and has a lot of brand recognition across the U.S. Obviously it's not in as close proximity to Silicon Valley, but it's not impossible to focus your job search on the west coast from Chicago (it's not easy though, and you'd need to be prepared to rely more on yourself and less on the career services office). I would recommend, if you haven't already, take a look at Chicago's placement stats: how many students or alum are interning or taking full time post-MBA positions at tech companies that you'd be interested in? That would probably be a really good indicator of how hard or easy it would be to make the transition from Chicago Booth to west coast tech. You'll have the skill set, but the question is whether you'd have the network you need to get recruited at one of those companies.
Did you apply to any other schools besides these two this year? Your overall results could also help you understand what next year might look like. From what you say, it sounds like you have a stellar profile and would be a competitive candidate at Wharton or Kellogg.
I'm sure you've already thought through all of this, but hopefully it helps you dissect it a little bit more. It's a question that only you can really answer, and it'll take a little introspection -- weigh your options and think it through, but trust your gut!