Well it sounds like you have a verity of things going on there. For starters, Anytime you have White smoke (really any color) you need to be concerned & find out what is causing it. White smoke typically means water (could be trans fluid though), start with that since it could be the worst problem/lead to other problems.
How did you "check for a blown head gasket"? Is/does the coolant level go down? When you say "blows White smoke" are you talking out the exhaust or this breather activity, both?
The 28 psi is normal for stock SBC's of that era, no concern there if you have adequate flow...If the rockers aren't rattling like a can of marbles, I wouldn't sweat the "oil thing" yet.
Are you sure the smoke coming out of the valve covers is White & not Bluish? Oil out the valve covers would be far more logical/common.
The mentioned coolant system pressure check/cylinder leakdown or compression test will likely lead you in the right direction.
As far as the timing goes...look the balancer over better, there has to be a line on it somewhere.
You will need to verify TDC on #1 & get the correct pointer (there are a couple different ones) .
The bog & backfire sounds like a yet another problem or Two. I wouldn't associate "bog" with timing, however the roughness could be. Report back & we'll try to help! Lorne