Setback 2: Insurance

Tom Cunliffe’s and John McKay’s experience of trying to insure their bikes varied.

Tom and Roz Cunliffe’s experience was very problematic, and for a while it looked as if they wouldn’t get insured at all. It was only through the dogged determination of the dealer they had bought Roz’s Betty Boop from that they managed to get insured at all – he spent hours on the phone trying to persuade Harley-Davidson Insurance to cover them.

On the other hand, John’s experience of insuring his Ultra Classic, several years later, was much more straightforward. This gave me some hope, but it was obvious that I would need an address in the state I was buying and trying to insure the bike. This gave a bit of a problem.

I had a handful of friends, or friends of friends, whose addresses I could potentially use – but not all of these were going to be viable for one reason or another.

Doreen’s good friend Bill in Billings, Montana looked a good option as it is so close to Sturgis, but Billings isn’t big and appeared to have only one Harley-Davidson dealer whose choice of used bikes wasn’t great – at least as far as I could tell from internet when I looked. It would be no good rockin’ up in Billings and not being able to get a bike.

Another potential option was my friend Thomas, but his situation was a little complicated. He was living in St. Paul, Minnesota, but staying and working during the week in Milwaukee, Wisconsin. Thomas had worked on my team in Edinburgh, and had only recently returned to the USA. When he’d joined us in Edinburgh, he’d decided to give up his place in Minnesota and to become a true nomadic consultant for a while – living out of suitcases in hotels. Having lived that life myself on several occasions, I know it is far from easy, but Thomas took full advantage of it, and spent his weekends and vacation time traveling around Scotland, England, Europe and even the Far East. After he returned to the states, he was immediately snapped up by a project in Milwaukee – as the good ones always are – but he hadn’t had time to re-establish himself back in Minnesota. Thomas was due to move into a new place in St Paul, Minnesota sometime around the time I was due to arrive, but it was going to be a bit hit and miss about which happened first – me arriving or Thomas getting his new place. It seemed just too risky to rely on Thomas’ move happening before I arrived to plan the trip on that basis.

Doreen and I both have friends in California who may have been willing to “loan” their address for my insurance, but San Francisco and LA are both a long way from Sturgis, and it was entirely possible that I would have to spend my first week or more, finding a bike and then sorting out the paperwork and insurance. My departure date had been decided by a series of gig and festival tickets I’d bought before knowing when my work commitments in Edinburgh would come to an end. Since these tickets were for Iron Maiden, Metallica, and Rob Zombie – some of my favourite bands – I was very reluctant to give them up. With these constraints in mind, I didn’t think I would time to get a bike and then make it from California to Sturgis.

The final option was Austin, Texas. Austin is also a long way from Sturgis, but Austin had something that San Francisco didn’t – my very good buddy Max!

Max is a legend with our crew in Edinburgh, and he was one of the very good friends I spent my last weekend in Edinburgh with. He’s a wild guy, who works incredibly hard, but parties even harder. He used play in punk rock bands before getting a grown-up job in IT. He also has a heart of gold, and is an extremely generous guy. Max had been working in Edinburgh for the best part of a year, but not with my team or client. I’d been introduced to him in a bar by mutual colleagues. I liked him immediately – and I’m sure that had nothing to do with the liquor we consumed that evening.

Max is a very well-traveled American. Austin, Texas was the last place in the US that Max had lived before coming to Scotland, and he still owned a house there. He also had a Harley-Davidson Road King there. As soon as he heard of my plan to go to the Sturgis rally, he said “Man, you’ve got to take my bike”. I admit I was a little reluctant about this idea – a Road King is quite a bit bigger than I am used to riding. But every time I saw Max he’d make the same offer. You cannot fault the guy for his generosity.

The fact that both Tom and John had been able to get insurance, and John relatively painlessly, gave me hope of being able to do similar, but I still had a gnawing doubt about insurance given Tom’s experience – I might not have a star of a dealer to help me sort it out.

As Austin and Max’s Road King were looking like one of the few viable alternatives, I bribed Max with lunch so that I could pick his brains about US insurance. Rather than rely on memory, Max said he was going back to Austin the following week to sort some stuff out – his house had been damaged by the fires earlier in the year – and he said he would talk to his insurance company, both about putting me on his insurance for the Road King and about insuring me in my own right for any other bike I might buy.

A couple of weeks later I talked to Max again about what he had found out. It didn’t look promising. In either case, Max’s insurance company would require me to have a US driving licence. I don’t know whether I’m better informed than John and Tom (in large part due to their books), or whether I am just plain chicken and more risk adverse, but I didn’t feel as if I was willing to take the risk of turning up, spending $10,000 plus on a bike, only to find out I couldn’t get it insured, and would have to rent. If nothing else, it would waste a precise week or two of the trip.

I’d pretty much made up my mind then that renting was the surest way forward, despite the expense, and that Chicago was likely to be the best port of entry.


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