In my experience, I have been able to park in the hotel lobby, basement or within sight of the front desk. The person at the front desk usually does not want your bike to go missing, so just ask (and use your gut to tell) if it's safe. If you must park on the street, it helps if there is a security guard you can recruit to your cause. Cable locks, disk locks or even a simple padlock through the brake disk holes are all deterrents. A cover is a huge help. A paid/secure parking lot or garage may be nearby.
All that being said, there are bad guys everywhere, and a determined thief will get your stuff. My philosophy is that there are two types of thief: The amateur/opportunist, and pros with tools, vans, friends and lengthy prison records. Do what you can to deter the first type, and hope you can make your bike invisible, undesirable or too risky a job to the second. Don't obsess, just do your best and sleep well at night.
Regarding insurance, you should be able to buy a policy at or near the border if it is required. Locals, truckers and other tourists are crossing those same borders every day, by the hundreds. Now visas, carnets and sometimes vaccinations can be a different matter and if you're lacking them, could stop you cold at a border.
Before enlightenment, change oil and adjust valves; after enlightenment, change oil and adjust valves.
SeanF screwed with this post 11-20-2012 at 12:14 PM