Some quick thoughts:
1. Take advantage of seomoz site crawler for issues sometime before going live- this will help detect any possible URL (duplicate) problems that are common in transition. Don't forget about redirecting any PPC campaigns you may have.
2. Based on experience, ranking will suffer in transition, regardless of preparation. If you spent time tightening your SEO metadata and structured your website exactly the same, you should see overall improvement after a few weeks. How quickly you are reindexed varies from one site to another. If you're seeing 20,000+ visitors a month, indexing should be relatively quick (that's just based off of my small statistical sample of personal experience.)
3. XML sitemap should be the current site you want to have indexed... not sure what you mean when you say you'd include the old site pages, which might lead to indexing problems no matter how you might work that out. With luck, your 301's will feed the wounded patient until Googlebot comes to stitch everything up.
If you could document your experience, it would be really helpful. Test and measurement = smart SEO

