Work backwards from adjudication rather than from the production calendar, and identify what can lawfully happen from Canada in the meantime.
Separate what needs presence from what does not
Hypothetical example: A good deal of a knowledge transfer does not require the person to be in the United States. Writing the protocol into the receiving mill's documentation, reviewing its kiln specifications, and preparing training material can be done from Chase as part of his existing employment. What requires presence is the hands-on commissioning and on-floor training, and that is the part that must wait for authorization. Building the schedule this way usually reveals that the pressure on the immigration timeline is smaller than it first appeared. It also avoids the temptation to send him on a visitor basis to do work, which is a different and worse problem than a delayed season.
Sequence the petition around the actual knowledge-transfer milestones and calculate time already spent in relevant classifications. Hypothetical example: A battery-recycling group needs a specialist for commissioning, but the engineer's earlier L time leaves little of the five-year maximum. The company should compare the project plan to the remaining authorized period before making travel commitments. A late discovery of the cap can turn a planned multi-phase transfer into an assignment with no lawful completion path.
Keep a dated record of prior U.S. classification periods. The remaining authorization is a calculation, not an estimate based on the employee's memory.