Of your two, I'd choose the latter -- implied order of an array seems like it will lead to problems. An alternative solution would be to require the admin to list the server twice. I believe the effect of listing multiple ports would be that the server would be in the list twice, and thus get 2x the selections than a server with 1 port. That would be obvious to someone listing the server twice, but, I think not obvious when "just" listing multiple ports.
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