Classic/Antique Car Repair: 74 nova problems, head gasket, combustion chamber

Question
Hello, I really need some help.  I have a 74 Nova with a 305 and Quadrajet carb.  The 305 was pulled out of an 89 caprice.  Bottom end of motor seem fine and top half was replaced with rebuilt heads and carb has also been rebuilt.  I have been battling with timing since motor was set and still might not have it right.  All right here is the problem.  Sometimes the car might just crank up fine an idle fine but then you shut it off and it might not fire back up.  It will sound like the battery is dyeing when I know it should have plenty of power.  Next problem, when it does start and idles fine and I let it warm up to temp you would think everything is fine.  Nope, you put it in gear and it just putts down the driveway very sickly and it might make it 15 foot, 30 foot if your lucky before it dies on you.  Next problem, When first start up I am getting moisture and white smoke out of tailpipes.  To be more specific I get white smoke out of passenger side and moisture out of driver side along with some backfiring out the passenger side. Can you help?  I am trying to restore this car on my own and I am no mechanic. Just learning as I go and yes this is my first restoration and I am trying not to get discouraged because I don't want this to be my last.

Answer
It's hard to do a diagnosis without doing a compression test and checking the valve timing, but I believe you have a bad head gasket or a crack in a head or block passage, because it appears that water is getting into the combustion chamber.  This can be very dangerous, so don't try to run the engine any  more. If there is enough fluid in a cylinder to balk the starter, you could have a nasty explosion due to hydrostatic lock.  Pull the heads back off and inspect the gasket carefully.  You should see evidence of fluid in one or more of the cylinders, that will narrow down the area you need to inspect. I'm not sure which side you'll find the problem on, so pull both heads.  There is a passageway under the carburetor which allows exhaust from either side to exit the driver's side, so the problem could be on the passenger side or the driver's side, or possibly both.

When you put the engine together, did you compare the head gasket with the old ones to make sure you have the right set, and did you have the heads and block surfaced to make sure the gasket would seat correctly.  Did you torque the heads in the right sequence, and to the right torque setting?

The lack of power is a different problem - I think your valve timing is not set right - go back and double check your work in assembling the timing gears.

Don't be discouraged by a few mistakes in putting together an engine - all of us had to learn by doing, and all of us made mistakes - some much more serious than what you are dealing with!

Dick