Both “when record enters a view” and “when record matches conditions” will re-trigger again — when the record enters the view again or when the record matches the condition again.
However, in order for the record to match the condition again, it has to unmatch the condition first. So unfortunately, in your situation, you can’t trigger the automation again by simply changing the dropdown menu from one of the matching options to another matching option. The record would have to completely unmatch the condition first, before you match the condition again.
One workaround for this would be to just create 2 different automations — one for each condition. Although Airtable has a paltry limit of only 25 automations, so that might cause problems if you create too many automatons (in which case, you would need to turn to an external automation platform such as my favorite Integromat.)
(Similarly, you could also do the same thing with “When Record Enters A View”, but once again, it would require you to create multiple different automations — one for each view.)