Ultimately GB would like to finish this season with the Arbor company, work on the rigs mid-winter, begin with the tourism company by next summer and be an arborist during the in-betweens all while becoming a permenant resident of Canada (dream big or go home?).
I was on my way to telling you that perhaps the Alberta Provincial Nominee program might be best for GB until I read the above statement.

It would involve a full-time, PERMANENT job offer so no galavanting around from employer to employer.
I'm assuming his current work permit is tied to a Labour Market Opinion and is closed to one employer. If that is the case and you apply to sponsor him through the family class, I agree with CharlieD that an overseas sponsorship is probably your best route for PR. He may have to keep his dreams of working for multiple companies on hold until PR is granted as there is no open work permit option for overseas applicants. That is only available for inland applicants and takes at least 11 months to be issued if first stage approval is received. However, applying inland with an open work permit application accompanying the spousal/CL app would keep him in status and allow him to continue working with his
current employer or for whomever he has an LMO and work permit with.
First thing to do is organize priorities. Then decide which route to take.