I went to the motorcycle show in Chicago and it got me thinking about motorcycle choices. Its something I get asked about often, since my bike of choice when riding around the Americas wasn’t something most people would pick.
In general, I give the same advice to everyone. If you have a motorcycle already, use that one. I mean, there are some bikes which aren’t suited to overland travel for one reason or another –

but in general any motorcycle can go on any trip, assuming the rider is willing to accept what that motorcycle asks in return. Cruisers aren’t the best off-road machines, but that isn’t the same as saying they can’t go off-road. The Haul road, in Alaska, can be a mess which has claimed its fair number of adventure bikes, but people manage it on their Harleys and Goldwings so clearly you don’t need a specialized motorcycle to make the trip. If you have a motorcycle you like, then ride it.
But lets say you don’t have a motorcycle and want to get something to travel on. First, you should take a MSF (or similar) class and get a motorcycle endorsement for your license. Once that’s done, you can start looking.
I rode and old, small motorcycle. Recently I’ve been using a new, small motorcycle. I like small motorcycles, and think using the smallest motorcycle (much like using the smallest luggage) you think you can get away with pays off in the long term. However, not all small motorcycles are cheap (in fact, the prices have been going up lately), and I think it’s more important not to spend too much on the motorcycle. You don’t what the investment in the motorcycle to cause a delay in the trip, or to result in too much anxiety while on the trip about the bike’s safety. I mean, you’re going to worry about it no matter what – but there is a difference between worrying about a $2000 motorcycle with another $1000 gear, versus a $15,000 motorcycle with $5,000 worth of gear.
There isn’t a “magic” number for how much you should spend – budgets are too varied for that – and personal preference does matter. Get a motorcycle you want to ride – since you are going to be riding it a lot – and get one that matches your level of mechanical ability. Newer motorcycle require less routine maintenance, but tend to need full garages when they do break down. Older machines require more regular work, but can be repaired just about anywhere (and I think they handle abuse better, but that is just my opinion and you can find a lot of those on the internet). If you are afraid of mechanical things and don’t want to have to touch tool while traveling – well – that is something you might have to work on.
So, breaking down the considerations for your overland motorcycle –
If you have a motorcycle – use it. Don’t spend the money on another motorcycle, when that money can go towards the trip itself, unless there is some compelling reason you can’t bring the bike you have (like you don’t own one).
Don’t spend too much on the bike. Reduce the investment to something you can, if needed, write off. If the bike has a major failure or is destroyed in an accident, don’t make that the end of your trip. Also, it will reduce the amount of stress you will have everything the motorcycle has to leave your sight.
Don’t stress over new/old or big/small. Any motorcycle can go around the world, and to most of the places on it. Get a motorcycle you like to ride, and then work out where you want to go and what you want to do when you get there. Somethings might be harder, but it will pay off for all the miles you’re on a machine you enjoy.