> I can spend a fair amount of money on this.

A charter flight would be your best bet. NYC to Paris will run you about $60-70k, that can accomodate about a dozen passengers so the cost goes down dramatically if you can find some people to share the flight (and the cost). Take a train to your final destination. If you bring friends or family with you, they can help with the luggage at this point. Bring as many pets or suitcases as you like - just inform the airline in advance. It'll be a very memorable experience too!

Many airlines allow small-medium pets on board, but unfortunately at 23kg (= 50 lbs) your dog is likely too big for that.