As Jalopnik’s resident car buying expert and professional car shopper, I get emails. . I’ve decided to pick a few questions and try to help out. This week we are discussing dealers that don’t honor deposits and someone torn between two lifestyle cars.

I was supposed to buy a new Jeep Wrangler right before Memorial Day weekend. It was an out of state purchase, and I was prepared to wire the money and pay for the car in-full immediately. On Friday, the dealer took a deposit of $1500 and said that the finance manager needed to call me to ‘go over’ some things. He called me on Saturday and I called him back immediately but never got in touch with him.

Monday rolls around and they inform me the car was sold. Can they do that? I placed a deposit and was committed to buy it. I suspect that once they knew it was a cash purchase they wanted to see if they can make some additional profit on it with someone else over the holiday.

I’m going to date myself here, A deposit, just like a reservation, is a professional courtesy—there really is no pure obligation for a dealer to hold that car, just like you are not under any obligation to execute the purchase despite placing the deposit.

In my experience, most dealers care about good customer experiences and will pull the car off the lot if a customer puts a deposit down with the intent to buy. Clearly, that isn’t the case with all dealers. You are probably correct that with an out-of-state cash buyer their chances to upsell you on whatever profitable add-ons the finance office would pitch were low, so they rolled the dice to see if they could make more money on that car during the holiday weekend. The gamble paid off on their end, and it’s a frustrating experience on your part.

Next up, who wins in the Gladiator versus Boxster battle?

I’m a working musician in LA. My kids are out of college and I can finally afford to get my dream car. I want a Porsche Certified, manual 2012-2016 Boxster but then along came the Gladiator... Probably the best looking truck of the last 15 years.

I currently have a 1999 Tacoma Pre-Runner 2WD Automatic and I love it. It’s my daily driver and what I take to gigs and I’ll never sell it. It’s pre-computer and I can do most of the basic maintenance myself although I do wish it was a stick.

I have come to realize that more than anything I really just want a convertible. My wife and I like to spend time in Big Bear and I LOVE the drive up to the lake and can only imagine what it would be like in a Boxster. But at the same time I think a manual Wrangler or Gladiator would be a blast in the mountains and with the low speed 1st gear I could even use it in LA traffic as a daily driver as well.

My budget for a used Boxster is 45K tops but with the Covid-19 no interest for the life of the loan and employee pricing I could swing a new Jeep.

Reliability is very import to me which is why Jeep scares me a little, but it would have a new warranty. Porsche Certified is 2 year unlimited warranty but their reliability is great.

I’m truly torn...

Your advice... 2012-2016 Boxster or new Wrangler/Gladiator?”

If you got the Porsche would you keep your Tacoma? If so, buy the Porsche...if not, think about how often you need to do “truck stuff.” If fairly frequently, maybe go for the Gladiator. If you don’t do “truck stuff” all that often and you are at the stage of your life where a back seat isn’t a requirement, maybe buy the Porsche. You can also just buy the Porsche to check that box on your bucket list, keep it for two years then trade it for a Gladiator. The depreciation will be not so bad on a used Boxster.

Got a car buying conundrum that you need some assistance with? Email me at [email protected]!

Updated 3/4/22 with new details.