How to buy your first classic bike
Triumph | BSA | Norton | Ariel | AJS | Matchless | For Sale | Motorcycle
▲ 1982 750cc Triumph TSX. This rare bike lives in Sump's garage and wouldn't be a bad choice for a first classic bike. The left-side gear change and electric starter might help riders of modern bikes to settle in, and there are enough classic bike quirks and (minor) issues to become familiar with, and even enjoy. The TSX "factory custom" is rarer and more expensive than standard T140s. So if you want a big Triumph twin, we suggest you seek out a standard (and cheaper) Triumph T140 Bonneville or TR7 Tiger.
Intro
Buying that first classic bike can seem daunting. But it's pretty straightforward provided you follow a few simple rules.
Buy with your eyes. That's where you begin. And yes, that sounds shallow and superficial. But you have to like the looks of the machine you're plan to spend any time with—unless you're buying it purely as a working tool, in which case you might be better off with something more modern. So check the FOR SALE adverts in the usual places (tip: start with Sump's Classic Bikes For Sale page). Then check the magazines, eBay, Gumtree, and/or attend a couple of motorcycle shows. See what takes your fancy. Make a list. Then move on to stage two. Which is...
...keep it simple. Can't stress this enough. Don't buy a motorcycle project, or a bike that needs repairs, or a sophisticated classic (i.e. something exotic with multiple cylinders and race-ready or similar). You might later discover that you just don't like the classic scene, and you don't want to be stuck with something expensive/exotic that you're unable to move on to someone else. And you don't want to be half-heartedly initiated into the classic motorcycle world with a few boxes of oily/rusty bits and only a vague notion of how to put it together. It can be deeply demoralising. So our advice is to start high, and keep flying.
Therefore, try these classic motorcycles first:
Parts are easy to find. Performance is good enough for modern traffic (with a 105mph top end if you don't mind the vibes). Maintenance is easy. Just check the prices. Avoid the cheapest. Look for sorted bikes, ready to roll. These are fairly easy to sell on—unless the market is really struggling, which occasionally happens. Just watch some ads for a few weeks and see if the bikes have shifted. Or phone up the sellers from last month or two or three months ago. See if the bikes sold.
Note that early T140s have a right-side gear change lever. Later ones have a left-side gear change lever. Does it make a difference? You tell us.
3. Any 500cc or 650cc Triumph twin. This means a 5T or 6T or Thunderbird is fine. We're still talking classic bikes, remember. So the Thunderbirds we're referring to are 1949 - 1966. Early ones (pre-1963) will feature pre-unit engines; i.e. separate engines and gearboxes linked by a primary case and chain. That's different to a "unit" engine whereby the engine and gearbox and primary drive are housed in a common crankcase, albeit divided into sections. The 500cc Triumph is a particularly good choice. Cheaper to buy. Better on fuel. Significantly lighter weight. Better fuel economy. Still plenty of parts. Right-side gear change only on the 500s and 650s.
5. Norton 600s are not too bad to source and maintain. Spares availability is not too bad either (except for tinware—but whatever you need is probably out there somewhere, and new parts are being manufactured from time to time). Expect to generally pay more for Norton twins than BSA twins, pound for pound. And BSA, note, are generally slightly cheaper than the equivalent Trumph (but not always). It's a fickle market with some selected models fetching "abnormally" high prices. Consequently, you have to study the market.
* Note that early British-built Bullets will almost certainly be significantly more expensive than Indian-built equivalents.
7. There are similar 500cc and 650cc bikes from AJS, Matchless and Ariel. Most of them are more plodders and rodders, but all are decent enough bikes. Just try the Eye Candy test. If you don't like the looks, look elsewhere.
8. If you want a lightweight first classic bike a 200cc Triumph Tiger Cub is a fair choice. It's a bit small for some, but is a nice bit of (very) mild hooliganism on an empty backroad (and no fun at all on faster carriageways). Or try a BSA Bantam if you want to begin with a classic two-stroke which are simpler to maintain and have a good spares supply (trickier with some tinware). Like the Tiger Cub, maintaining them is no problem for the averagely bright owner/rider. But you'll be riding around at 45 - 55mph thereafter. Right side gear change only for the Tiger and the Bantam.
Japanese classics
We suggest that you look at the Honda CX500, the Yamaha SR500, the Yamaha 650 (bit pricey now), the Honda 400-4, the Honda 750-4 (also a bit pricey), the Kawasaki Z series (some of them very pricey; less so for others). And you might try a Yamaha RD250, or an RD250LC, or a Suzuki GT750 triple (pricey), or a Kawasaki H2 750. A 1,000cc or 1,100cc Suzuki Katana is still a great bike and is fairly easy to live with.
Beyond that, there are dozens more. As a general rule, look for bikes that were popular in their day. Don't splash out for rare machines or unusual machines. Leave that to the experts or buyers who know exactly what they want, possibly to add to their collection. Practically all Japanese classic bikes have left-side gear change levers.
American & European classics
If you particularly want an European post war classic, you're probably looking at BMW or Moto Guzzi. Both can be very rewarding, but the spares supply is patchier, and once again there aren't so many people readily at hand with expert knowledge. However, the classic bike community is international, and there's always the internet. Help is out there some place.
Buyers guides
When you've finally selected a bike, or perhaps a couple of bikes, you might consider picking up a buyers guide. Some are better than others. But pretty much any of them is worth a tenner or two. These guides might not tell you everything that can go wrong with a given motorcycle, but they'll invariably warn you about the really important stuff. And that could save you hundreds if not thousands of pounds/dollars.
Read. Study. Question. Use the guides and ask questions. Don't be afraid to admit your lack of knowledge, but don't over emphasise it. Tip: take a copy of the guide when visiting the bike and let the seller see that you've been studying the "form". Might help.
Classic shows
We'd recommend that you visit a couple of shows and just hang out for a few hours. Pretty much all classic bikers are friendly. They'll talk forever about their wheels, and most will be happy to impart advice. Check the autojumble stalls. Ask what tools you might need (Whitworth? AF? Metric). Watch people starting bikes. Ask about the procedures (friendly bikers, remember). Talk to club members at club stands. They're always looking for fresh blood.
Test rides
You might wangle a test ride on a cheaper classic. But understandably, many owners won't want you riding their more expensive bike without seeing the full purchase price in their hands—and classic bikes are often more "precious". That said, by the time an owner gets around to selling his machine, some of the "shine" has been lost. Just keep in mind that plenty of classic owners will change their mind at the last moment and refuse to make a deal. And we've known one or two classic bike owners who've gone to great lengths to re-purchase their pride and joy.
But should you buy without a test ride? You'll have to decide that for yourself. But you should at least see the bike being ridden. And make sure you see the bike warmed up properly. Check for oil leaks before it moves (ideally from cold). Then check for oil leaks after the bike is fully warmed. Most classics leak a little. It can be stopped, but it takes a lot of time, energy, money and skill. We can live with a little oil dripping here and there. It's no big deal—unless you're big into environmentalism. But perfectly dry classics are rare.
Beyond all this, usual buying security advice applies. Take a friend. Ideally a BIG friend. You'll want to check your insurance conditions. Check around the bike as best you can. Remember that plenty of classic bikes feel very odd at first, particularly those with a girder front fork. But such bikes will all be pre-war, and you're advised to leave the very early stuff alone until you've got your classic bike wings.
Finally, owning classic bikes can be very rewarding. But it takes a little time to fully adjust and possible downsize, especially if you're used to high-powered, slick-handling modern sports bikes or roadsters.
Meanwhile, check our page our regularly
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9. Japanese classics have long since become popular. But proportionally, they're rarer. At least, it's rare to find a very good, unmolested one. Most examples were scrapped (often prematurely), crashed and still awaiting repairs, and/or neglected by owners who kept them for decades in garages or sheds or beneath tarpaulins. Yes, that happened to many Brit bikes too. But Brit bikes were oilier and were more heavily built and could take more abuse. Jap classics are often made of thinner materials and not "born to last".
Spares can be a problem, and largely because of that Japanese classic bikes are usually more expensive to buy and restore than British iron. Rust is your biggest problem.
10. American and European bikes are a little more complicated for first time buyers. American classic iron isn't as expensive as it used to be; not comparatively, anyway. But you'll still need deeper pockets, and you might not find quite so many helping hands on the British side of the pond—although there are plenty of people with good knowledge of post war Harley-Davidsons and Indians. The spares supply is also excellent. But still, it gets just a little more complicated, and the 
initial outlay will likely be more. Shovelhead Harley-Davidsons and Ironhead Sportsters could be a good starting place. Both need a "constant" hand, but both are fairly easy to work on. Note: the Ironhead Sportster can have serious vibration issues. So longer rides could be painful. But short hop riding isn't usually pretty good fun.