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 - An Old-Time Tractor Demonstration - by Kim Pratt. Sam was born in rural Kansas in 1926. His dad was a hard-working farmer and the children worked hard everyday to help ends meet. In the rural area he grew up in, the highlight of the week was Saturday when many people took a break from their work to go to town. It was on one such Saturday in the early 1940's when Sam was 16 years old that he ended up in Dennison, Kansas to watch a demonstration of a new tractor being put on by a local dealer. It was an Allis-Chalmers tractor dealership,
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