Your "UPDATE" section isn't too complex so making it work with MT should be fairly simple. I'd suggest making a temporary folder on your server, set up your MT version of UPDATES in this temporary folder and then tweak the MAIN INDEX Template until it looks like your existing pages. I would think you could copy and paste the MAIN INDEX Template into Dreamweaver and tweak away on it. Then paste the HTML back in when you are done. The template has tags between the normal HTML tags that tell MT where to place your content - you'll probably figure it out just by looking at it.
When all is well, point it to your normal location and remove the temp folder/files. Good luck and have fun!
Make sure you backup or convert all your existing entries! If you have questions, this forum is a great place but the manual is also very well written.