1) Best way to redirect all new URLs sitewide
Page to Page redirects is the best solution, even though it's a major pain. I would take a look at your traffic data for at least the past 90 days, possibly even further, and create a 301 map from every page with inbound traffic to the correlating page on the new site.
2) The prudence of heavily editing product listings at the same time of redirecting the URL (i.e. updating product descriptions)
If you're up to it. However if rankings drop then you won't be able to track it back to a particular change.
3) Site structure: Should I strive to keep the new site link structure as similar to the old as possible?
If the current site structure converts well, then maybe you should stick with it. The nice thing about switching to a new platform is it's a great opportunity to reinvent your site if you feel like it needs it.
4) Resources or guides on transitioning a site from a SEO perspective
This article might be a little dated, but it should point you in the right direction. http://www.seomoz.org/blog/10-things-relaunch-your-website
Good luck!