This spring, when Oksana mentioned that she finally had things under control enough at work to consider a vacation, we sat down to decide where we could go. She could afford up to three weeks off, but that didn’t necessarily restrict us. With almost any country in the world as an option, we had to narrow it down from not only what we wanted to see, to what we wanted to do.

Oksana, for her part, was focused on diving. As far as she was concerned, we were going someplace sunny, warm, and underwater.

Me? I’d been thinking about buying a new car. My ’89 Jeep hasn’t been weathering the winters very well, and we can afford to trade up. I’m not in the market for a new new car; I can’t see spending that kind of money when I don’t even have a garage. Something a little younger than 20 years would be nice, though, and buying a used car from somewhere dry should minimize the risk of an getting rusty “Juneau body.”

I didn’t tell Oksana, at first, that I was considering shopping for a car while we were on vacation, because she would have pushed for buying it from her employer, Mendenhall Auto Center. That would have been fine, except the more I thought about it, the more I was starting to look forward to another road trip.

Combining these two goals limited our options somewhat.

We picked Florida. Not only could we buy a car and dive on a reef, we could also visit my grandparents!

As our departure date neared, our plan coalesced:

Step 1: Buy one-way tickets to Florida.
Step 2: Spend up to one week with my grandparents, shopping for a car.
Step 3: Put the car through its paces on a drive to Key West; spend up to a week diving the reefs.
Step 4: Drive across country either leisurely or like a bat-out-of-hell, depending on the time we had remaining. Barge the new car to Juneau from there.

It went… more or less according to plan.

Before we bought tickets, I called up my grandfather to run the idea by him. He was excited. Excited that we were coming for a visit and excited that we were buying a car. I didn’t realize it at the time, but he was to become a valuable resource in our search for a new vehicle.

With gas prices nearing $4/gallon, he was surprised that I was in the market for a new Jeep, especially since we’d have to drive it from Key West to Seattle – just about as far apart as two points can be in the continental United States. I explained to him that gas prices weren’t too much of an issue, because once home, I wouldn’t be putting many more miles on it. .8 miles to work, .8 miles home, maybe 10 miles here and there for lunches and grocery shopping; I go 2-3 months between tanks of gas. My previous Jeep has served me well, so brand loyalty had me shopping for a newer-model Grand Cherokee, but I wasn’t opposed to looking at some “crossover” vehicles like the Honda CR-V or the Toyota RAV4.

Besides, with gas prices so high, there were dozens of news stories about Americans trading in their SUVs. It was a buyer’s market.

While I casually browsed through car auctions on eBay and Yahoo, my grandfather pounded the pavement. The extent of my research before we left amounted to flipping through a Consumer Reports at the dentist’s office (which had me questioning the Jeep brand’s reliability over the foreign models) while he was out talking to dealers, digging up relevant information such as Florida (maximum elevation: 345ft) not being the best place to look for 4-wheel drive vehicles and my $10,000 ballpark limit being reasonable for what we hoped to buy – an up-to-5-year-old SUV, 4×4, with a preference for options over low mileage. Within a day or two, he already had a line on more than one Jeep for sale. I appreciated the help, but had to assure him that I couldn’t commit to anything before we could see it for ourselves.

On June 8^th, Oksana and I flew into Tampa. Exhausted, waiting an extra hour-and-a-half for our luggage because a thunderstorm had sent the baggage handlers’ inside for an extended coffee break, I worried about the week to come. Oksana was in the middle of her penultimate MBA class and planning to be on call for work throughout the entire trip; I wanted to make sure that, when she returned home, she felt like she’d been on vacation. Shopping for a car can be a stressful endeavor. Shopping for one under a deadline, more so. I hoped for the best.

And the best was what we got!

Jetlagged, we slept in a bit the next day and got a late start. My grandfather told me that his brother, Lynn, had a lead on a Jeep in St. Augustine. In fact, Lynn thought it was such a good deal that he put $500 down on it to make sure it didn’t sell before I’d had a chance to look at it. First thing in the morning, first lead of the trip, that was hard to hear. I appreciated the sentiment, but I wished he’d talked to me before putting his own money down. The last thing I wanted was to feel obligated to buy a car I didn’t want.

We called Lynn up, made some plans. St. Augustine was a couple hours away, so we decided that we’d hit a few dealerships along the way, see what the market was like. Even if we found a fantastic deal, we promised to hold off, at least until we’d seen Lynn’s find.

My grandfather drove Oksana and me around and we stopped at three or four dealerships. We didn’t limit ourselves to just Jeep dealers, either, as we figured just about any dealership would be taking SUVs as trade-ins. It was true. Each lot had at least one or two Grand Cherokees, and plenty of similar vehicles for us to browse. We glanced at some CR-Vs, RAV4s, Muranos, and even peeked at an older model Mercedes. There were certainly some in our price range, but none with four-wheel drive.

And that seemed to be the big problem. Every dealer had something they wanted to sell me, but nothing with four-wheel drive. Beginning to doubt the plan, I remarked to one salesman, “Yeah, I guess Florida’s not the best place to go looking for a used 4×4.”

“On the contrary,” he replied. “Any 4×4 down here has probably gone completely unused. It’ll be in pristine condition.” It may have just been the guy trying to make a sale, but it gave me hope.

With time in the day running out, we decided to drive the rest of the way over to St. Augustine to take a look at the Lynn’s Jeep. At least we knew it had four-wheel drive.

After a little socializing and catching up at my uncle’s house, we drove together to see what he thought was good enough to put $500 of his money on. It was at the local Dodge/Chrysler/Jeep dealership, which didn’t bother me, but posed a bit of a problem for Oksana: “My coworkers will never let me live it down if you buy a car from another dealership!”

As it turned out, Lynn had bought at least three Jeeps from this same dealership, Atlantic Dodge, and knew the lead salesman well. When we arrived, he introduced us. There wasn’t much beating around the bush; with money down already, we were simply handed the keys and told to take it for a test drive. We barely had time to look at it first.

First impressions were good, however. It was a surprisingly blackish Jeep for Florida – “Graphite” on the outside, black leather on the inside. There were just a couple, minor scratches in the paint job, and hardly any marks at all in the interior carpeting and upholstery. It was a 2004 model Grand Cherokee Laredo, about as new as we were looking for as both Oksana and I disliked the body style changes they made the next year. Sunroof, premium speaker package, power seats and mirrors, and – bonus! – heated seats. The only real hesitation was the number of miles on it: 69,000. Not bad for 5 years in Florida, but the same car in Juneau would have been hard ridden, indeed.

So we took it out for a drive. Felt like a nice ride, about what I’d expected. After warning my three passengers, I gave it the hard brake test. Also, the get-up-and-go test, from the stoplight. Had to say it didn’t feel quite as strong as my old Jeep, but still more than adequate. We found ourselves an empty parking lot, and I pulled over to make sure the various four-wheel drive positions would engage.

While slowly tooling around the parking lot, Oksana used her cell phone to call her own dealership. We didn’t have internet access available to check the Kelly Blue Book value, so she was asking one of her coworkers to run the numbers through the dealer system. Was it a decent deal at $10,000? After rattling off all the options and the condition the car was in, she reported back with the only hesitation: The high mileage would hurt its resale value in Juneau.

Well, I wasn’t looking to resell it. Long story short, when we got back to the dealership, we bought it.

Of course, buying from a dealership is never a short process. There were papers to sign, payment methods to discuss, hands to shake. We got held up a bit when Oksana began pressuring them about sales tax, registration, and all the things she knows about dealership sales from the accounting side. We also spent some time discussing the best form of payment. We settled on our out-of-state personal check, but my uncle had to write one of his own to cover it just in case ours didn’t clear within ten days. $10,301 was the total. I may be wrong, but I think that’s the single, largest purchase I’ve ever made.

One anecdote worth sharing: Oksana didn’t immediately let on that she also worked for a Chrysler dealership in Alaska. In response to many of my questions deliberately asked in an attempt to get more for my money – “What about that little plastic piece that’s missing on the hatchback?” “What about the empty tank of gas?” – our salesman replied (more than once) with, “Look, I don’t know what kind of business they do up in Alaska, but we run an honest shop down here. This is a 5-Star Chrysler dealership. You’re getting a $14,000 car, with a warranty, for $10,000…” He always stopped short of saying “don’t push your luck,” but he constantly reassuring us that he wouldn’t be making any money on this deal as a favor to a long-time customer, my uncle.

Well, at one point, while Oksana was on the phone again trying to sort out what the total cost of the plates and tags would be once we returned to Alaska, the salesman, making small talk, asked me what I did for a living. I tried to explain to him my digital-internet-computer job thing at the university, and we’d just about exhausted the topic when Oksana got off the phone. He casually turned to her and asked, “So, what do you do up in Alaska?”

Oksana locked eyes with him and was quiet for a moment. If this were a movie script, her pause would be perfectly represented by a “beat.”

SALESMAN

So, what do you do up in Alaska?

OKSANA (beat)

I’m the comptroller for a 5-Star Chrysler dealership in Juneau, Alaska.

Our salesman, across the desk, stared back at her. (Beat). You could tell he was trying to decide if she was pulling his leg. Oksana, with a small smile on her face, simply stared right back.

“No…” he said. “Really?” He honestly didn’t know what to make of her.

“Yes.”

“But you’re so young!”

“Been the comptroller for 4 years now,” she replied.

They went back and forth a few more times. He was incredulous, she kept reassuring him. Eventually they fell to talking about their respective dealerships, the current economic conditions, and other corporate mumbo jumbo. Then she got a tour of the place and met a bunch of people while I waited around for the paperwork to be completed. Seriously.

Presently, everything was squared away. A temporary paper tag was taped to the back window, we received two sets of keys and a handshake, and we were out the door and driving along behind my grandfather as he led us back to his house in Beverly Hills.

I couldn’t believe it! Less than 24 hours after landing, we’d already bought a car. Now we could sit back and enjoy our vacation!