Dynamic, Content Driven Page Height & Best Practices Positioning

I’d make this two posts, but I think my problems might be related.

Dynamic page height: If content (set up in divs) is within the same container, shouldn’t the page grow to accommodate content? Three weeks of searching WP forms and documentation and the web, but I am still missing something.

Positioning: I’d prefer all the areas to flow using floats, but have had to set hard margins to place content reliably. The green callout box (.callout) in the vertical center of the page places fine in Firefox but ends up at the bottom of the page in IE8. Additionally, the footer should be 75px below the content on every page.

The site is at:

URL: https://0055ae0.netsolhost.com/wordpressLR/

Pastebin links as follows:
CSS: https://wordpress.pastebin.ca/1747598
header: https://wordpress.pastebin.ca/1747600
footer: https://wordpress.pastebin.ca/1747602
index: https://wordpress.pastebin.ca/1747606
page: https://wordpress.pastebin.ca/1747603

Thanks in advance for any help you can offer.