By Daiwiskers
Others on here have more experience than me with these engine's but here's my thoughts on this
Was the primary chain jammed when you removed the cover it could have jumped then jammed removing the cover could have freed it off any swarf in chaincase? would point to a loose primary chain if all good in primary my next look would be the oil pump worm these have been known to strip after just one kickback any whear on the splines replace the worm and drive with a british one from our host fragments from the worm should get caught in the timing case and hopefully not get to the crank
Hopefully you will have found the problem by now but if not take off the pushrod adjuster cover check clearances if still all good Off with it's head and barrel piston failure is not unheard of as has been mentioned earlier
To be perfectly honest if I was running a Indian built engine I would upgrade piston and oil pump as matter of course just for piece of mind
Hope that makes sense Dai
By TexasChris
Again! more interesting information! Thank you!

In the short time I've had this bike running it has kicked back a number of times (not all the time, but a good number) if this is known to cause oil pump issues, then that could be the narrative that's leading to my problems. I haven't had chance to start digging into this yet, but I think my first step is loosening the rocker oil feed lines as suggested and checking if I am getting oil circulating. If not, oil pump seems a likely culprit of a cause. then the head will need to come off to assess what damage it might have caused.

While i'm waiting for time to get stuck in (and i'm stuck at the office) any info out there on what causes the kick backs? are they less "dangerous" with the upgraded Hitchcock's pumps?

Thanks again folks, great information and discussions here, really appreciate it.
By TexasChris
Answering my own question by further reading of Hitchcock's Tech notes...

BAD TIMING: Another cause that we have seen a few times is a badly timed engine that back fires or kicks back when starting. In fact this happened on one of our new built competition engines whilst testing a new ignition system. On the first start up we had a fairly large back fire which resulted in stripping a brand new spindle instantaneously. Be warned! Other causes for backfiring are air-leaks, weak mixture, starting technique etc. - sort the problem sooner rather than later.

...I have had plenty of back fires and kick back recently while dialling it in, so seems very likely that the oil pump/spindle maybe have taken a beating.
By Daiwiskers
Checking for oil feed can be done a few ways unfortunately they are all easier with the engine running
Remove dipstick check oil is returning to the tank it can be seen returning on the right hand side of the dipstick tube
Remove the push rod adjuster cover you will see the oil returning down the pushrod tunnel
And the old favorite way of loosening the banjo bolts for the rockers ( be careful you can quite easily bend the pipes when you loosen them) however our host's do a excellent set at a reasonable price but if you're careful and support them when undoing them you should be OK if you do loosen them just crack them open a bit you don't need to take the bolts right the way out
Above all there are some good guys on here that will be able to get you through just about anything on the bike
Cheer's Dai
By PeteF
Don't be too concerned about the oil pump, my 350 has kicked back many times over 20k miles without a problem.
Yes, it CAN cause damage but not as much as people sometimes say in my experience.
Worth checking though. You should get oil at the rocker banjos pretty quickly even just turning the engine over.
By TexasChris
Hey everyone,
Snuck a little time with the bike and some tools. Topped up the oil and cracked one of the oil line banjos loose...and it fired up 2nd kick and almost instantly had oil flowing (at a pretty decent rate!) out of the loose banjo! Doesn’t seem like an oil circulation issue to me!
I’m thinking I should do an oil change and valve clearances this weekend and try to do a gentle ride on it? Maybe this is nothing to do with the engine?
By Daiwiskers
Sounds like a plan to me if it seized the damage is done so you have nothing to lose take it easy and see how it goes
Bump starting a 500 single is not going to be easy especially if you changed down
Take it easy see how it goes
Good luck with it Dai
By TexasChris
Haha yeah the rolling bump might be a bad habit from racing. I race flat track on a Rotax 600 single, and if you stall that getting sketchy in a corner, it bumps starts back to life pretty easy. But we do have them geared up for high revs on short tracks.

I hate not finding an obvious CAUSE of something like this, but I also don’t want to tear apart a motor apart looking for trouble. What do they say ‘if it ain’t broke, don’t fix it’.

Who knows I might be back in a few days with some more disasterous symptoms! Haha
By Daiwiskers
Let us know the outcome
Happy to try and help but do like to know the outcome
Cheers Dai

Shop for accessories at Hitchcocks Motorcycles