I feel uniquely qualified, if not somewhat compelled to address your request.
First, Microguy, you read like a public service ad advocating the importance of pursuing a full life, rich in diversity. Though we've so very much enjoyed your views on .Pro, surely you deserve more. So may I be the first to wish you good fortune as you pursue a more appropriate calling...
I spent some two months in the Philippines, most of it in Manila. I had to be dragged back to the States by my then-wife, and all but lost my job and head. The country and its people are lovely. Manila is hot in many ways. And, yes, I own both in .Pro.
I own numerous city.pro and citypro.com domains. That said, I must state, with much reluctance, that neither form tends to represent a great investment. There are exceptions, of course. But they are few and far between. As to city.pro domains, my reservation goes to the issue of nexus. At the very least, there are several other tlds that fit better. Even so, if we see an increase in the development of websites likes "oahu.pro", I would expect like domains to rise in value. Ironically, its hard to find another word extension that fits better with .com, than pro. This is where Andrew's stats speak the loudest. If only, however, we weren't still discussing a geo-domain...
All told, I would appraise at low to mid xxx. Good luck!