So my stepsister won a 2016 Camaro for $50

I entered to win a ZL-1 Camaro once. My wife said that if I won I would have to decline because taxes and insurance would cost too much. Good thing I didn't win, I would have missed her.

A lady that works with my MIL wins all kinds of stuff doing this. Cast a wide net every day, and you're eventually going to win.

I'm on Jerry's plan. I spend my sweepstakes time on GRM forum and I'm pretty sure it's negatively affected my wallet over the years.

M2Pilot wrote:

Enyar wrote:

M2Pilot wrote: In reply to STM317: Yes, you have to pay taxes if you take the cash option. I took the cash option when I won the M235i last year. It was a $42.5K car & taxes were withheld from that. I got a check for approx. $30K & a federal tax form (not a 1099) titled "certain gambling winnings", that documented value of car & taxes withheld. When I filed tax returns, the $30K was reportable as gambling winnings but I could deduct the cost of raffle tickets & any other gambling loses from that. When I won the Range Rover it was from a sweepstakes. There was no cash option. I paid state sales taxes & registration fees up front & received a a 1099 tax form & had to pay taxes when I filed returns. When your stepsister files 2017 tax returns, she may be able to modify the amount stated on her 1099 if she can demonstrate that the value of the car is actually less than MSRP. If she can document that like equipped camaros were retailing at a less than MSRP she might save a few bucks. Copies of ads, rebate offers, etc could help if she chooses to take this route. She might take it to Carmax or whoever & get an offer to buy in writing & use that figure to modify amount on 1099. I'd get a tax professional to help me on this. Congratulations to your stepsister. This may not be a car any of us lust after but it's a nice windfall for her.

Um...you won a M235 AND a Range Rover? Gambling addiction or great karma? Details?

I spend 15-20 minutes a day entering online sweepstakes. To some, this may seem to be a strange way to "waste" time but I've won some nice prizes. There's no cost except time to this. The Range Rover was the grand prize in a sweeps sponsored by Greg Norman Wineries. I do occasionally buy raffle tickets if the prize is something I think I'd really like & I like the sponsor & number if tickets is limited. The M235i was won in a BMWCCA Foundation raffle. I took the cash option on this one & put the money with some of my money & got a Euro Deliver on a '16 M3. I'd probably have taken the car but I wanted another M that was a sedan.

What's your junk mail/spam/telemarketing situation like? Seriously, I'm really wondering.

Do you have to pay the tax up front on this, or is it just due at the end of the year like a regular return?

If I had to pay up front I'd probably just take the cash and call it done. If I could pay with my regular return I'd go through the trouble of trying to resell it.