I apologize for any inconvenience.
For the geotargeted content, if you have contacts that have custom fields with information you can insert that, but it's not really geotargeted unless you set that up within their details.
I have taken a further look into the situation and I do see that the GIF file you have does work within Constant Contact. It also works within Google and Yahoo as well. As far as Outlook is concerned, it will always render as a still image for anyone opening the email in Outlook as GIF files aren't supported in their client. Unfortunately this is really out of our control as they are their own entity.
I can assure you the countdown does work properly within Constant Contact and will within most Email clients as well, but unfortunately Outlook will not be compliant with that file type. Here is a link to some insight as to common email display issues broken down by email clients and what they support!