re: Royal Enfield Motorcycles

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Second issue is that I know literally no one that has a motorcycle or would be knowledgeable about it. Should I stick to a new bike in that case?

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If you have no option but to do this on your own, here's a few things to look for.

First the easy stuff:

Check the tires for wear and signs of being plugged or otherwise compromised. Also check for dry rot if the bike has a few years on it with little mileage. You'd be surprised how many used bikes with low miles have dry rotted tires. Motorcycle tires are right up there in price with auto tires if you buy quality rubber and unless you know how to remove the wheel, get the old tire off and mount and balance the new tire, expect to pay at least $100 for a shop to do it for you. Oh, and don't even think you will get over 10K miles on a rear tire and about 20K on a front tire. They wear out way quicker than auto tires.

Check brake shoes/pads for wear and rotors for damage. Rotors and pads are easy since they are exposed with many bikes having them front and rear while some bikes have rotors and pads on the front and drum and shoe brakes on the rear.

Check fluids if the bike has hydraulic brakes and clutch. Check the levels and see if they are fresh and not old. Also check engine oil levels.

If a chain drive bike check the chain for wear and tear and excess slack in it.

Easiest of all is to check for dings, dents, scrape marks in the stuff that is not suppose to hit the road. That will tell you if the bikes been down.

If the seller allows you to do a test ride by yourself, go through the gears and listen for a strong running engine with no misfiring or throttle hesitation. Also feel how the tranny shifts----is it smooth, clunky, miss shifts, etc. Some of that can be your fault not being familiar with the bike so take that into consideration.

Ask for maintenance records. I do my own maintenance and everything I do is written down in my owner's manual as to date and what was done and how many miles were on the bike when the work was done.