Hey guys,
Thanks again for all the great tips! I think personally I'm more concerned about high mileage due to my limited resources/knowledge of maintaining bikes. I've got a buddy that rebuilds OLD bikes and he's offered me his 1969 BSA Thunderbolt or his 1966 Triumph TR6 for a good deal rebuilt...but I'm concerned that once something goes I won't be able to repair it and be stuck! Beautiful bikes too!
There is quite a difference between a high mileage bike and an old bike. The sound, look and character of an old bike is intoxicating. But, they do need love and attention from their owners in order to enjoy them. You don't have to know how to do a major tear down and rebuild but, having access to someone that can show you how to deal with maintaining, diagnosing the issues that are bound to occur is a must. Knowledge and experience with ignition/electrical, carb/fueling, oil/lubrication systems, brakes, clutch etc. would be neccessary to have a pleasurable ownership/riding experience of those older machines.
I'm not much of a wrench but, I have performed some basic maintence myself with the encouragement of some very knowledgable friends/riders. It can be fun and rewarding when you do more than simply turn the key and ride.
But it can be a nightmare and discouraging if you don't know what you're doing and have no one to help you keep things going. The Internet can help but, there is no substitution for having access to someone that can show you.
IMO, I'd look for something within the last 10-20 years that has been ridden and maintained on a regular basis and you feel confident the previous ownership demonstrates this.
I bought a 10 year old Sporster after considering a Bonnie. It cost me $5000 and had less than 10,000 kms. But, being parked or not used very much, it still needed to be freshed up. Swapped out all fluids. Fork oil, brake fluid, new brake pads, engine and primary oil, plugs etc.
Knowing some other owners that ride their machines on a regular basis and keep them maintained very well, I'd have no problem buying a bike with what others may consider high mileage.