What a cute CUTE puppy! At 2 - I love the wise eyed puppy you've become - just beautiful! 
Hlo buddy , if you not go there yet then i want to tell something.
Due to the current COVID situation, a lot of the limited pet routes are not even flying. Working on getting a dog into the US right now. Domestic lines are not flying animals at all and the International lines have limited airports. I think five; JFK, Chicago, Dallas, Seattle, and one I can't remember.
And cargo shipping will not be also an option as other members are also saying that.
You need to check status for ground shipping. Check any service provider who done that in one go.
Check Citizenshipper ground pet shipping and get enquiry about your condition.
One thing is sure that you can let your lenny in airline with 22lbs. I can feel your pain.
Check other options otherwise you might have to leave him or cancel your program
Hope you get good alternative.
