1 - The version of the theme on the site is NOT responsive, and when I upgrade to the newest version, it removes all the custom formatting done on the site
2 - I didn't originally design or build the site, so all that custom formatting must all be done again when I upgrade.
It sounds like you're applying your theme customizations directly to the original theme file. This can cause a number of issues, including losing your customizations when they update the theme.
I would highly recommend migrating your theme customizations to a child theme instead. Child themes allow you to modify, or add to the functionality of that parent theme. A child theme is the best, safest, and easiest way to modify an existing theme, whether you want to make a few tiny changes or extensive changes. That way you can ensure you have the most secure and up-to-date version of your theme while retaining your customizations.
Here are a few more links that will explain the benefits of a child theme and a walkthrough on how to set one up:
http://codex.wordpress.org/Child_Themes
http://premium.wpmudev.org/blog/create-wordpress-child-theme/
Switching your customizations to a child theme would be the easiest way to get your site and front page customizations to be useable on mobile since you could upgrade your theme to the newer, fully responsive version and would eliminate the necessity to further hack your theme and plugins (including Jetpack).
Let me know if you have any questions.
