As Jalopnik’s resident car buying expert and professional car shopper, I get emails. Lots of emails. I’ve decided to pick a few questions and try to help out. This week we are talking about getting deals on two cars, when the best time to sell privately, and minor accidents on certified cars.

First up, can a dealer give a better price if you are buying two cars on the same day?

Both my father and I are in the market for lightly used/CPO Cadillacs. Him, a 2017-2019 Cadillac CT6, 3.0 or 3.6. Me, a 2016-2018 ATS-V manual.

Now, my question is, what is the best way of going about this purchase in order to get the best deal? Should we work on getting the price down on one car first, then throw in the “how about we buy another car right now” as incentive for further discount? Or should we just be up front and say, “hey, we will buy two cars off of you today, let’s make a deal?”

There is a common misconception that dealers can leverage extra discounts if you are buying two cars. While some folks will tell you they got a better deal because they purchased two on the same day, the reality is a good dealer is either going to give you a competitive price or they are not.

Whether you are purchasing new or used, there is a floor at which a dealer can’t go any lower if they are serious about moving a unit. Buying multiple cars doesn’t change that bottom dollar. Dealers don’t have access to an additional discount mechanism like a rebate or something for an additional car purchase.

In this particular case, it gets tricky because you are getting two used cars one of which is fairly rare, the ATS-V manual, so the likelihood of both cars being on the same lot is very slim and even if they are on the same lot either car might not be the right specimen for the given buyer.

Because shopping for a used car is really focused on the I would suggest that you treat these as two individual purchases and plan accordingly.

The internet has changed the way cars are bought and sold. It’s now a lot easier to figure out who…

Next, is there a best time to sell a used car?

Have you ever written about the best time to sell your car? Just curious as I have a 2016 Outback Limited with a shade over 60,000 miles. The car is in very good shape and I owe about $8,400 on it. Is there an ideal time to sell this if I want to get something else?

There are two ways this question can be interpreted. The first way could be referencing the best time of year to sell a used car. While some folks will say it’s harder to sell convertibles in the winter, something like a Subaru Outback is going to have a fairly consistent market year round. If the car is priced right you should have no problem finding a buyer.

The other way could be, is there an ideal mileage or age range that would maximize your sale price? The concern here is that while cars get older and rack up the miles, the value goes down, but the longer you drive the car without payments the more value you get out of that purchase.

There are really no hard and fast rules to when you should sell your old ride, though if the repair costs are becoming a regular occurrence it may be time to move on. I recommend driving it as long as you can until your circumstances dictate you are ready for an upgrade.

Finally, is it still worth buying a certified pre-owned luxury car with a minor accident on the history?

I found a nice 981 Boxster with the right options and more importantly, the right transmission (#savethemanuals). The car is also CPO’d by a Porsche dealer which is a huge plus given it’s a 2013. Here’s the issue: The Carfax shows a “minor accident” in the form of a rear-end collision. The dealer was very forthcoming and said the rear bumper cover was replaced due to a low-speed impact, but was replaced and inspected by a certified Porsche technician and is as good as new. However, given the damage was over $500 to replace, it has to be reported on Carfax.

They have lowered the price a tad under what other Boxster of similar model year/spec are going for, but the car is otherwise in great shape. Am I screwing myself on resale for this Carfax blip down the road? Or should I take the good deal, enjoy the comforting security blanket of 2 years of warranty, and hit the road?

There is always a bit of hesitation about buying a used car that has an accident report because you never really know the full story. Usually “minor accident” or “damage report” on a CarFax indicates cosmetic damage, that being said you may still want to get.

It’s a small investment but having a third party take a look may reveal details that either the dealer didn’t know or didn’t disclose, the inspection could also indicate that the damage was indeed minor and the repair was quality.

When buying a used performance or specialty car, a pre-purchase inspection is key. This is true…

As for the resale situation, cars with a damage history (regardless if it is minor or not)are going to be worth less from a resale perspective than cars without that mark. However, if you are paying less for it now, that should balance the scales even if you get less for it later.

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