By noting the position of the timing mark on the damper vs. the position of the pushrod, you have documented a timing problem. Now you have to determine whether the damper ring has moved [and the relationship between the pistons and the valves is actually correct], or whether there is a problem in the timing chain.
To determine whether your timing mark on your damper is correct, Google "positive stop method" + "TDC"...this will determine exactly when your piston is at TDC, and whether or not there's an error in you damper timing marks. If there's an error, these guys can repair it:
http://www.damperdoctor.com/
Then with a correctly marked damper, check where your intake valve is in relation to TDC. If your cam still appears to be significantly retarded, tell your buddy that he needs to suck it up and replace the timing chain and gears.
Anytime you do an overhaul on a smallblock V8 and don't replace the timing chain and gears, you're doing a "half-fast" overhaul, and are at best postponing the day when the engine will let you down. Is the price of a chain and gears worth bent valves and pushrods, or perhaps sticking a valve through a piston top? Call it insurance, replace the easy stuff, and walk away KNOWING that those parts are good, rather than guessing.
P.S.: The poor vacuum readings are a sure clue that the valve timing is off, Sherlock.
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Today's Featured Article - Field Modifications (Sins of the Farmer) - by Staff. Picture a new Chevrolet driving down the street without it's grill, right fender and trunk lid. Imagine a crude hole made in the hood to accommodate a new taller air cleaner, the fender wells cut away to make way for larger tires, and half of a sliding glass door used to replace the windshield. Top that off with an old set of '36 Ford headlight shells bolted to the hood. Pretty unlikely for a car... but for a tractor, this is pretty normal. It seems that more often than not they a
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