The easiest way to go about getting a job on or off base in Okinawa would be to go through
American Engineering Corporation first. They do a lot of engineering tasks, to, I believe, HVAC installation and repair.
As your wife is a Japanese national, you will fulfill the first requirement of having a valid Japan visa as you will presumably be under a marriage visa, allowing you to work both on and off base in two different capacities.
Fortunately for you, you are coming from a country — Canada — that allows you to
convert straight over to a driver's license issued in Japan, forgoing the rigorous paper and driving testing process, which many locals and foreigners still fail several times. That said, you must be able to prove that you have driven in Canada for a minimum of 90 days. Supporting evidence of this is a valid Canadian driver's license, a school training certificate, pay stubs that showed during those 90+ days you worked, and therefore had to drive to get to work, a driving background check, rent receipts, and anything else that you think is pertinent to prove that you have driven there for that length of time or longer.
Even though it is much cheaper than attending a driving school, upwards of 300,000 yen, as well as taking the tests, quite possibly multiple times costing more and more each attempt, it's harder to prove those 90 days than one would think.
I eventually got mine converted after showing multiple documents of what I would consider concrete evidence, going back to high school transcripts (certified, stamped, and signed by a school counselor 10 years after the fact). It cost me about 8000 yen to convert, all said and done; but, it was about 5 visits over a month to two to verify if document X worked, document Y, and so on. The tedious task of proving those 90 days will be worthwhile as it will save you a lot of money, still giving you some heartache, as each visit can be scheduled out weeks apart. This will fulfill AE's second requirement of a driver's license in Japan.
While there are jobs on base that you qualify for as a Japanese employee on base (MLC/IHA), these jobs are particularly hard to get and could take several years to even land an interview or selection. Therefore, you should apply for those once you get here and if the offer down the road is better than AE, take it up because the long-term benefits will be great. Additionally, you'll work alongside American personnel, to include military and civilians, in the desired field.
In the meantime, I would shoot off a resume and application to AE (linked above) to see if you qualify for a position, or can get your foot in the door, prior to moving from Canada so that you don't find yourself in a rock/hard place and can easily transition. Otherwise, you could be setting yourself up for failure without having a job lined up and have to rely on low paying temporary staffing positions, which isn't the best pay, nor the best working conditions.
If you don't mind the nitty-gritty of cleaning home AC units, one can make 5000-10000 yen per home unit cleaned. Doing it fast enough and lining up the work yourself, you could take home a hefty profit in a single day by just cleaning 6 units in 2 different homes.
Good luck
. I've seen some equipment installed in the craziest locations when we were in japan last. 
