Hi raintrek,
I don't have any advice to offer unfortunately as I have limited knowledge when it comes to the visa process and the processes you are talking about in the Philippines, but I just wanted to wish you all the best and good luck with your situation. I think we all know the feeling of being separated from the one you love and having stresses about visas and protocol that we feel are outside of our control.
Actually I have just had a thought...have you approached a visa agency in the Philippines to get some advice on the matter about whether your fiancé can leave the country with debt still hanging over him? I used a company called Wise Visa Agency based in Manila to help my fiancée (then girlfriend) get a travel visa earlier in the year. I wouldn't advise you letting them prepare any paperwork as they were pretty poor in that area, but they were very knowledgeable about the process and offered good advice. They also have an office in London, and the staff there were very friendly and I could call them with any questions I had from here in the UK. Send me a PM if you want their details and the name of the contact in London I used to speak to regularly, he was invaluable to me in getting information and preparing for our visa.
Good luck!!