Looking Ahead to Drupal 4.7

Most website's I run will be easily updated once Drupal 4.7 rolls around. In fact, the average website won't need to be updated anytime soon. But for one website in particular, I am already having nightmares. I need to upgrade for a few reasons:

• I need the extra functionality. There are new features in Drupal 4.7 that will maker certain tasks remarkably easier. For example, the new block regions. More than 1,500 pages all have the same footer in the content area. The owner wonders why she can't change how it reads on all of the pages every now and again (once a month or so). Isn't that the advantage of a CMS? Now it is.
• My buddy Jeremy is working on a new Ads module. I have been requesting development on the current banner module, which prompted Jeremy to re-write it as an Ads module. The fundamental difference being that ads will be nodes, thereby increasing functionality and enabling the sort of options I am looking for. I am finding myself in GREAT NEED of said increased functionality - the ability for ads to be searchable, and/or matching option, list all option, etc.
• I am splitting the content (some 1,900 nodes) into two websites and need to do a lot of cleanup. Not a technical issue, but a real one nonetheless. We are facing some real branding and marketing issues which require us (meaning me) to completely revamp the website as a whole. This includes structure, navigation, taxonomy, etc.
• I want to use some of the new goodies. There are some needed modules and/or module improvements that I see in the repository. I think they will be very helpful to reach my goals for this website.

The headaches come in when I figure that I have some 27 contributed modules (Amazon Tools, Flexinode, Simplenews, etc.) and would like to use another 12 (E-commerce, Blog Theme, User Points, etc.) at least. That's not including some modules I'd like to discard (FCKeditor) in favor of others (TinyMCE). At least I don't have to worry about Menu on the Fly anymore.

There are two possible approaches.

1. Take the site down for a day and upgrade the usual way. Fool around with the terms and menus, un-publish nodes, whatever - as I go along.
2. Redevelop the site on my local machine using UniServer and swap a clean, brand-new 4.7 website for the other in the dark of night.

I will have to consider this some more.