please advise... processing work permit in Japan

Hi!! I'm so glad i found this forum because my husband and I are in of opposite opinions the best way to proceed... sorry this might be a long post...

My husband works as an IT system analyst/developer in Japan and has been granted a TRV to canada, he has an aunt there. While there, he plans to look for an employer willing to process the requirements needed for him to be given a work permit. However, his working permit in Japan will end on Oct 2009. My questions are:

1) Is it possible to get or process working visa/permit while he is Japan? It is in my understanding that work permits can only be processed outside of Canada.
2) Will he also need POLO approval?
3) I'm assuming he won't have to go through the usual POEA pre-departure process since he is already an OWWA member. Would it suffice if he gets an OEC from the philippine embassy, then proceed to Canada under his working visa? What would be the difference of acquiring the visa outside the Philippines and if you are coming from the Philippines?
4) He will be leaving to Canada on April 2009, start looking for an employer, then will probably stay for a couple of months only, maybe until July then he will go back to Japan again while waiting for LMO or work permit. My argument with him is that he should re-apply his working visa in Japan first, as a foolproof precaution, before proceeding to Canada. Would two to three months suffice for him to look for an IT job? It was my opinion that he should secure his visa in Japan first so he can enjoy his 6 month stay there, without worrying that he needs to renew his Japan visa. What would be the best do you think?

Thanks for your suggestion and help!