Hello friends,
Me and my girlfriend are from NZ and are planning a 6 month motorbike trip two-up through South America later this year. We are slowly learning what planning that requires.

We're new to motorbiking so its a big learning curve, we think at this stage we will get a v-strom 650 or maybe a transalp.

But, the question I have is in relation to motorbike insurance while travelling. We are a bit worried about spending all the money on a bike and gear and then having it stolen or having an accident, so we want to insure it on the way.

Is this possible?
Is it the way to go?
Some info I have read says you buy insurance at the border of each country. Has anyone done similar?

Thanks in advance.

Regarding the insurance for stolen bike , a good chain is the best investment you can do , it will be almost impossible to find an insurance that will cover it in all South America, for accident its pretty much the same but what you should have, its a personal health/accident insurance that will bring you back home or cover your medical expenses ( make sure they cover road accident on motorcycle ) , for many parts of the world a moto insurance is only a way to get money from tourist and it can be bought at border crossing.Some EU company have special plan for RTW trip but cost a lot of money and I will very curious to see how good they do when you have a claim form an accident in place like Guyana or Bolivia......

An insurance is essentially a contract between two parties so you can find an insurer for almost anything...but it will cost you, dearly.
I would say you can get the insurance you want for roughly 30% of the value of the bike, per year.
Depending what model your bike is, not many people will have an interest in stealing your bike. The most plausible scenario would be someone using it in the country side, so actually some small towns are more dangerous than big cities in relation to bike theft.
I dragged a 5Kg chain from Texas to Buenos Aires, and I think I did used it once. Then on a subsequent trip from Mexico to Panama on a BMW, I learned the lesson and carried no chain at all.
Just do not leave your bike in the street overnight. Never. It does not matter if you have a chain or insurance, if someone steals say the carby, you are stuffed. So do not leave the bike outside.
And if you crash it badly as to be unrideable, just thank your lucky stars and go home, end of trip, done and did it.
There is ample information here and other places in regards to your question. Part of the kind of travel you are embarking on involves proper research. If you are going to go around asking every single question that pops in your mind, by the time you are ready to leave you will be 80 years old.
PS Transalps are quite common in South America henceforth the possibility of having it nicked totally or partially is higher than other bike models