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I haven't repaired an HD case but I have used helicoils on other brands with great success. Preparation, patience and careful application are all required for a long lasting repair.
Personally I think that you are screwed, the heli-coil is a good idea and maybe the only choice. You have to ask yourself where all the metal shaving are going to go when you drill and tap for a heli-coil.
Might just try chasing the threads with a tap coated in grease first. I understand(never tried) the grease will hold the metal shavings onto the tap. And if you are just chasing the threads it may not actually cut any new material from the case, just straighten out what is messed up. Use a bottom whole tap because I don't think there is enough room between the case and flywheel for a regular tap to go through.
Also after trying that apply liquid teflon tape to the plug, this should plug any leaks.
All predicated on the hole not being tottaled.
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I would get a new plug and wrap it with teflon tape. I worked on a pipeline for years and have seen some really bad threads that would hold 1400# pressure very well with teflon tape installed. I bet you will be fine. Just get the fairly heavy tape and pull it really tight down into the threads about 2 or 3 wraps should do. If not, add some more until it does.
All of the above are great ideas, try them first. If it works then its good, if not then you will have to spend some money. Did you strip them tightening it down, or when you tried to start it??
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The threads in the case are cashed. Started it straight but I must have overtightened it and they all pulled out. They weren't in the best shape to start with. I realize the only way to do it right is to split the cases. Don't have a problem doing it but I haven't bought the tools yet. What do it absolutely have to have to do the job? If the bearings are good can I reassemble with the existing bearings or will the outer be damaged when I press the crank out of the left case? Is a case splitter and pressing tool from like Jim's better or is it better to use a press? Thinking about putting a stroker crank in while it's apart. Whats the quality like on the Ultima cranks? Do they need to be trued before installation? Thanks for all the responses.
if the above does not resolve your problem:
consider measuring the size of bolt at NAPA auto parts or similar and maybe a self taping oil drain plug could be modified: like sawing off/removing the magnet from magnetic kind