You probably need to adjust your valves. Ironhead Sportsters are equipped with solid lifters and must be adjusted with zero backlash. If one of the pushrods is adjusted just a bit tight and holds a valve open even slightly, the bike is almost impossible to start with the kickstarter.
To adjust the valves, the bike must be stone cold. Take the spark plugs out, raise the rear wheel of the ground, and put the transmission in fourth gear. Turn the engine over by bumping the rear wheel in the normal direction of rotation. Bring the piston of one of the cylinders up to top dead center on the Compression stroke. Pop the pushrod tube covers and check the pushrods. You should be able to spin both pushrods with your fingers. If not, adjust the pushrod so taht it's tight. Then back it off to where you can just spin it with your fingers. Keep in mind that on a Sportster, it's better to have the pushrods slightly loose than tight. Once you get that cylinder's pushrods adjusted, do the same thing with the other cylinder.
Now, once you get this done, starting your bike is simply a matter of figuring what works with it. I've always said that kickstarting a Harley, especially a Sportster, is a ritual. Some bikes like for you to milk the throttle twice, kick the engine through twice with the choke on and ignition off, then turn on the ignition and kick it. Other bikes seem to want only one milk of the throttle, one kick with the ignition off, and then kick it. Each bike seems to have it's own particular ritual that you must figure out to get reliable starting. I'd try milk the throttle once, put the choke on, kick it through with the ignition off once, then turn the ignition on and kick. If the bike spits back through the carb, you need to start all over again. If you get the engine flooded, hold the throttle wide open and kick until it fires.
One other thing about a Sportster. Did the old man you bought it from have a limp in his right leg? A Sportster is notorious for "slipping through" when you try to start it. The result is that all your weight comes down on your knee without any resistance. The result is your knee tries to bend backwards, the way it wasn't designed to do. This can tear ligaments and cartilage in the knee and it even has it's own name, "Sportster Knee". Be careful.
Ride Safe
Steve
THANKS, STEVE. AS SOON AS MY KNEE STOPS HURTING, I GUESS I'M GONNA TRY TO ADJUST THE VALVES LIKE YOU SAID TO. I NOTICED YOU SAID TO KICK IT THROUGH ONCE WITH THE IGNITION OFF. I'VE BEEN KICKING IT THROUGH TWICE, OPENING THE CHOKE, MILKING IT TWICE, TURNING THE IGNITION ON, & THEN KICKING THE HELL OUT OF IT (TO NO AVAIL). MAYBE I WAS JUST DOING SOMETHING WRONG & DIDN'T KNOW IT. WHO KNOWS ? BY THE WAY, IS THERE ANYTHING I CAN DO ABOUT IT "GOING DOWN THROUGH THE FLOOR" ? MY KNEE WOULD REALLY APPRECIATE AN IDEA ON HOW TO FIX OR PREVENT THIS.
Don't get too hung up on how many times I tell you to kick it with the ignition off. The point was that it seems like each bike has it's own special way to get it started. You have to figure out what this way is.
You can fix the "through the floor" thing by replacing the kick starter ratchet on the backside of the clutch shell. One part of the ratchet is riveted to the backside of the clutch shell and the other piece is a sliding gear type piece that is on the mainshaft. Part numbers 33379-71A & 33432-73. The first number is the ratchet and the latter is the ratchet gear. You probably will not be able to get them through your local H-D dealer. They are available aftermarket through V-Twin Manufacturing as reproduction parts. You'll have to pull the clutch out of the primary to replace this stuff but it's not too hard. Just keep in mind that the nut that holds the clutch shell on the mainshaft has LEFT-HANDED THREADS in it. If you want an exploded view of the setup, contact me off forum at [email protected]. I'll scan a picture and send it to you. But, still, even with new parts in the bike, this can still happen. The reason is once you bring the engine up on the compression stroke and go to kick the heck out of the thing, as you "jump" on it, you inadvertantly release the pressure on the kickstarter. This allows the ratchets to come up on top of the teeth instead of being locked into them. Then they slip. OUCH and a whole bunch of foul language. Get someone to help you get the bike back up off the ground. Those little teeth are just 3/16" deep.
Kicking the motorcycle is an artform in itself as well. I have a 1965 FL that I still use the kickstarter on. It was the last year of the panhead engine and the first year with electric start. Thus the first year of the ElectrGlide. It has an electric starter but I never use it. On your Sporty, the way I would start it is to put my left knee up on the seat, bring the engine to the compression point with my right leg, the come off the seat with my left knee and kick the engine over. I learned to never "straddle" the bike to start it. On my low compression '65, I just stand on the right side of the bike and push the kickstarter down with my right foot. No jumping at all. BG>
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