I have a new problem. I fixed the problem with the piston hitting the valve. Now every thing turns over great. The starter works great until I put the plugs in. It cranks, but sounds like the gear somewhere is popping out. I took off the side cover and see no sign of a stripped gear anywhere.
Could it be a bad bendix gear or starter motor ? Not sure where to look. I did buy a new solenoid that sits next to the starter. Could it be bad? Thanks

 

Please include the year of your IronHead in your post. Which side cover did you take off, left, right? Without more detail it, from your description it could be the bendix or associated mechanical parts, but i am not very good at those parts. It could be a weak battery, given that it cranks fine with the plugs out.

These two Factory manuals are necessary for working on these bikes ...
99484-?? Service Manual
99451-?? Parts Catalog
The ?? is one of 69, 78, 85 depending on the year of your bike. Put the number into the Google and eBay searches or buy from a local HD Dealer or indie motorcycle shop.

 

Ok thanks, The bike is an early 73 sportster. Battery is new and fully charged. I started by resetting the cams correctly, switching the rear piston so the notch faced the intake. That fixed the piston hitting the valve. Nothing is bent and has great compression. Put it back together and replaced the stater solenoid(electrical one next to the starter motor). Everything spins freely by hand and when using the starter without the plugs installed. When cranking with the plugs installed it makes a very bad noise like gears slipping. I took the left side cover off and looked at all the gears and none are broken, So it makes me think the bendix is bad causing the noise when it slips in and out. The motor does turn over while doing this, but sounds terrible.
I am new to harleys and would just like to know if I am going in the right direction, or if I missed something obvious. Thanks

 

I think you may be on the right track. It sounds like maybe the bendix is slipping under the increased load of full engine compression, with the plugs in.

To test the bendix, lock the bendix body in a bench vise, then carefully use a large set of channel lock pliers to grab the gear and try to turn it in both directions It should turn in one direction only if it's good. Use a pad of some kind to keep from chipping any gear teeth with the pliers. If the gear turns at all in both directions, the bendix is bad.

Another possibility might be bad starter motor bearings that make noise under a heavy load. But I'd check the bendix first.

 

Ok Thanks, I do know how to work on engines and what not. I have taken apart many, many engines of all kinds, just not familiar with the harley stuff, Yet. Thanks for the help.
The bendix does move in both directions under a pretty good twist with some channel locks. Plus I found a worn out needle bearing in the starter housing while I was in there a bit ago.

 

Did you get the bendix changed out and get it to turn over correctly?