Perhaps it is possible to get all your cars free by leasing them through your business, but I really question the reasoning on disposing of large sums of money on exotic "business" living that could be allocated elsewhere - even after paying taxes on it.
Nothing's free, since you're paying for it out-of your's or your business's accounting. One way or another, it's costing you money, even if at a reduced tax rate. Nothing's free.
I worked for a time in sales training for a very big earner when starting out in sales. Although he earned big, he was totally obsessed/fixated on "write-offs." He continually claimed; "he made too much money, and that if he didn't spend it by writing it all off, the Government was going to get it all!" What a misguided individual that guy was - making the equivalent pre-tax of close to $500K a year, and spending it all. He would spend and gamble on lavish Las Vegas and cruise vacations year after year, claiming they were all write-offs. When he died of old age, his estate was worth zip, his wife had to borrow for the funeral, move out of the pricey rental home, which he did not buy a decade and a half earlier, because he never had any money because he had written it all off. He was driving an old POS American car. Really a sad situation.
Over the years I've run into other self-employeds that live very high off the hog. At times, some mention they need the write-offs because they're making too much money. I just take a deep breath, and roll my eyes when I hear that schpiel coming. I've learned that if you don't write so much off, you will have more money to fund your retirement spending years with cash.
