timing the application, and from inside or outside?

Hello I would like to get some advice about the best way to proceed.

1. My husband arrives in Canada in February as a visitor.
2. In May (as long as it is approved like last year) he will have his status changed to a temporary worker valid until October. His work is seasonal and traditionally gets an approval with LMO etc. The company has agreed to hire him again as such.

Should we apply for his residency OUTLAND as soon as he arrives in February/March. Or also with OUTLAND do we wait until his status has been changed to temporary work permit since changing the status requires leaving and re-entering the country.

OR should we apply INLAND so that we can apply for an open work permit and hopefully have it approved by the end of the year and if so do we wait until before or after he applies to change his status to "temporary worker" again because he'll have to leave and re-enter the country (flagpole).

Thanks for any advice or suggestions!

K