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I can't answer question one. I don't know what type of cars you've owned previously to help answer your tax question. I believe you must pay the total tax for the car up front in NY (based on the length of the lease). I purchased my vehicle and paid around $4800 in tax in CT (7% for purchases above 50K).
I believe in NY your tax rate would be 7.5-8.5%? The total of your lease payments would be around $31,824. The tax on the total of those payments due up front would be about $2550 at 8%. That number is extremely close to the number the the dealer is quoting you. HOWEVER, I think the dealer (Not David or Francesca) is trying to pull the wool over your eyes. The tax payment they are quoting you is most likely the total tax for a vehicle purchase and not a lease. This makes the $2250 in credits they offered you useless. I think they fluffed the tax number to eliminate the credits they offered you. The credits should be deducted from the purchase price prior to the tax. With that said I would just buy the car from Ryan Amico or David Avilles. I think Ryan can have the car delivered to your house. In David's case I would take a cheap Southwest flight from Bradley International, CT to Maryland and drive the car back to NY. You will put a nice dent in the 1200 mile break on the ride home.
Good Luck!
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