Media Rich Custom Fields?

I was checking the plugin, Advanced Custom Fields, it is pretty neat.

Now, let’s talk about our custom fields, not the ACF plugin.

Do you know, besides the shortcodes, if there is a way to get info to appear from, say a PHP database with images and data, connected to the custom field selectors?

If we have a custom field that gives us a selecdtion and then we enter firstly by letter or by name, a selection, for example, of a name of a restaurant with its image and link in the selector part of the question on the add listing page. Could this info automagically appear? How can we do that efficiently?

Also I see the geolocations has flags, but can the countries as selectors have flag images appear when you select a country? And is there a way to put the US and Canada as the first two countries? Then the rest, alphabetical?

Our custom fields in PPT are great for data, how about making them media-rich in the question part of the custom field of the listing and also the answer of the custom field of the listing? Is there an easy way?

Thanks.