@Welfare, had to break up the paragraphs; it was pretty hard to read. Are you planning to lease/finance through the manufacture (ie: Toyota/GM finance) or third party financing?
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Originally Posted by welfare
The sales guy says if that's my plan, best option is long-term lease then buyout early when it's time to sell. Reason being is that I'll only be paying tax on each payment rather than the entire vehicle.
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That is correct; you are paying taxes on the amount of car that you are leasing. For example, if you are leasing a $50k car and residual value is $20k, then you are paying taxes on the $30k through monthly payments. At the end of the lease contract, you can pay the $20k plus tax to own the vehicle.
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Originally Posted by welfare
As I understand it, third party buyout relieves me of paying the tax. And if the third party is a seller with pst number, and shipping it down south, he also isn't required to pay it. That sound correct so far?
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Not quite sure what you mean by relieves you from paying tax. If the someone buys out the vehicle, they pay the tax on the buy out amount. For example, you've made 6 payments of $1000, for $6000 in total assuming interest rate of 0%. They would pay $44k plus tax and whatever buyout fees.
IF the third party has PST number, they STILL HAVE TO PAY TAX. All they do is claim it back from the government.
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Originally Posted by welfare
Are there any disadvantages to achieving my objective through leasing over financing?
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Depends on the lease or finance contract and whatever fees are associated with breaking the contract. I would personally be wary about doing a lease and having a third party buy it out in 6 months.
Usually with most vehicle purchases, you're highly underwater with negative equity so you could be potentially stuck with a depreciated asset even with factory leasing programs.
Negative equity is when you owe $50k but your truck is worth $35k. Please don't be that guy who's stuck with a money pit.