Help with view styling - template/css/whatever
To show fields you have to use views_php where you can check

if ($row->field_hide_track) {
    print $row->field_track_icon;
}
For filters you are on the right track you are showing terms as checkboxes you just have to style labels of the field just like DrupalCon Denver's site something like this.

views-exposed-form-schedule-page .form-item-edit-track-1 label, #views-exposed-form-schedule-page-1 .form-item-edit-track-1 label, #views-exposed-form-schedule-page-2 .form-item-edit-track-1 label {

background: url(/sites/all/themes/denver2012/images/track-1.png) 0 0 no-repeat;
}