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How about making a lunette eye hitch extension/converter for the front of the trailer - quick attach to the kingpin of the trailer? I am sure the wreckers pintle hitch is up to it.. NB. This a purely an idea. Extension of 'frame' to the left of the pic, then chaining to trailer frame would...

Hey Red - how are you going to mod the hood for the Jakes - speed hump or raise the whole thing on taller sides?

What did you do to stop the truck rolling forwards/backwards or sideways off of the outriggers since they are not rigid? Did you just cross your fingers and hope the fixed baseplate would be good enough?

Red - have you tried to slide apart your new boom support legs yet? I recently tried to get mine apart with the winch + snatch block on my 916A1 and braced to the back of the lowboy - no go. Need to come up with a new, more powerful plan - they have been soaking for 2 years... I think I am...

I've done a rebuild thread for both level winds (which do a wonderful job when working) - they are easy enough to strip and service, even a little modification if appropriate grease fitting is missing. Spare parts will be the issue if you cannot rejuvenate the damage. Though stuff like felt...

Valence. Welcome to the big bad world of wrecker restorers.. I think you are starting out ahead of the curve - I would much rather have your situation of civi neglect than civi butchery if your destination is a good example of a military 816. So many were bought and civilianised by amateur...