If your primary question is can one create multiple blocks of text and graphics, make changes to one block and have the other blocks auto fit the page, then YES:

Use the "Push" function for each block, use Fixed Inside for text within a block (font size remains the same) and Repel Text Under for any graphics, animations and videos. By using the push function the page length automatically extends to accommodate the content length. The only action you need take is to resize the edited block to accommodate the changes in content.

Click image for larger version.  Name: Push Function.jpg  Views: 58  Size: 118.8 KB  ID: 125811

- I want the box to auto-adjust to the text -(either bigger or smaller) and as there are about 20 boxes -
Your site http://www.TheRavenswoodGroup.com does not look to have 20 boxes though; were it to extend to that number it would likely be better to have the boxes as separate pages and the export the site as a supersite, with page headings and page links on the index page. This would reduce load times and make it easier to manage the mobile variant.