His hot breath stinking of garbage that to my knowledge he hadn’t eaten, my dog pushed still closer from his awkward perch on the passenger seat and once-again dry-heaved. I flinched yet again, trying to push him back over to his side of the rental car whilst keeping one eye on the road — which I couldn’t see through the torrential downpour we’d driven through for the past three hours.

The date was July 7, 2015. The trip was my initial move to Costa Rica. The dog and I had been sent ahead as the advance team.

The dog-entry saga had started several months before when I learned that my airline would gladly charge an amount just south of a first class fare to fly our dog to Costa Rica. As an unexpected wrinkle our dog would also require a Costa Rican customs broker to enter the country. My airline did not provide this service, but gave me the number of their local office in San Jose with the idea that they would be able to source one for me.

Over the next few days I called the airline’s San Jose office and listened to a never-ending series of rings. Eventually I called their US office and let them know that they might want to independently verify that they indeed have a San Jose office. This led to a series of non-productive suggestions that felt less like help and more like an attempt to wear me out so I’d choose another airline or turn my dog loose in the woods and forget the whole idea.

I eventually abandoned the other failed avenues and began calling the airline’s San Jose office once again. To my surprise I reached a nice lady after the second ring. We quickly concluded in Spanglish that she didn’t have any information on customs brokers — but had heard of them and would call around on my behalf.

I phoned her back several days later and she physically passed the phone to an individual — who worked one desk over — who announced that he was a customs broker and part of a team of brokers housed in this same office. I decided to forego asking several burning follow-up questions and instead got his e-mail address so I could send him the specifics for my trip.

I sent the e-mail a few moments later, only to have it immediately rejected. I called the San Jose airline rep again and asked her if she can please help me get a valid e-mail address for the customs broker. Through the cupped receiver I heard her muffled conversation with the customs broker seated a few feet away. Seconds later she spelled out an entirely different e-mail address for me (same guy, but a different company).

There were no rejections this time around. There was also no response. I sent several follow up e-mails over the next few weeks with no luck. This was the first of many occasions where I pondered a peaceful future that didn’t involve a dog.

My bride soon saved the day by finding a customs broker via Facebook (which I didn’t use at the time) and I managed to get everything squared away with this new resource. Two days later the long-forgotten first customs broker sent me a random e-mail confirming that everything was handled — but asked that I resend him all of the details as he wasn’t sure he’d used the correct information.

Many weeks later I arrived in San Jose and asked the off-site rental car agent for directions to the airline’s cargo facility. The agent ended up calling my customs broker and getting directions, which proved to be roughly 63% accurate.

I parked at the end of a long series of buildings at what I thought was the entrance. I learned via some nice guys smoking out front that this was probably the right spot. One of the guys even passed me his phone with a contact queued up for me to call. The contact was, of course, the initial customs broker who’d ignored me until I’d hired the other guy.

“No,” I said, “Not that guy. A different broker.” My do-gooder looked very confused and said that this was the guy that brought in all of the animals.

I was neck-deep in this hole of a conversation when a random guy walked up and asked if I was Mr. Cobb. I agreed that I was, and he introduced himself as my customs broker — then asked if I could give him a ride over to another part of the facility.

We drove through another series of streets labeled “no entry” and wound up in front of a loading dock  located inside a 15-foot tall fence clearly marked “stay out.” I looked at the broker, who waived his hand dismissively and encouraged me forward.

I drove in to the mostly empty loading dock area and a gentlemen who looked quite official ran out shaking his head and waving us off. I looked to my broker and he shrugged again and indicated that I should back-in like the big trucks.

By the time I was done backing-in the warehouse official was at my windshield. He wasn’t happy, and when he realized that yelling at me in rapid-fire Spanish wasn’t getting him anywhere he turned his wrath on my broker, who looked like he was about to take a nap. Eventually, with a quick look at my passport, the anger disappeared and we were just three guys hanging out at a loading dock.

My broker pulled his phone out of his pocket and said he’d call the airline. Within a couple of minutes an airport baggage cart containing my very freaked out dog was sitting in front of us. We shook hands with the official and I freed my dog from the kennel and got a leash on him so he could move around a bit before our long drive.

My broker then produced a couple of sheets of paper, one of which was an invoice for $403. Cash. This was about $75 more than his estimate and my surprise was obvious. He leaned in and volunteered conspiratorially, “You know about $125 of that is taxes.”

This meant that the other $278 covered his work in printing the invoice as well as the 30 second call to the airline. I didn’t have any singles so he graciously agreed to call it an even $400 and walked off to his office – which may or may not exist.

With fur flying around the interior of the car, my dog and I soon found ourselves stuck behind an endless series of 18-wheelers as we tried to make our way to our new home. The dry-heaving started about an hour in to the ride, which ended-up taking close to five hours. I stopped several times and let him out but all he wanted to do was get back in and blow hot garbage breath on me.

I learned a few valuable lessons from this effort, including: 1) next time around buy a dog that fits under the seat, and 2) don’t volunteer for the advance team.