Piston Failure

I got my heads milled, ended up taking 0.010" to get them flat. also got my rockers shimmed perfect while I had the heads off.
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I put everything together and now there's a few things:

1) There's been a slight leak at the rear drivers side the past few times I've had the head off. I usually remedy this by a bottle of bars block sealer and the problem is solved. I switched the heads around to the other sides and even with the heads milled and switched, it still trickled. Bottle of sealer fixed that though. (I really suspect block deck issues now)

2) Fixed that small persistent issue, idled up to temp a couple of times. No leaks, no smoke- good to go. Drive around the block (~5 miles, warmed up and hammered it a little). Got back home and there's coolant residue on top of the timing cover and running down the drivers side. Wiped it clean.
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Borrowed a cooling system pressure tester and pressurized the system, it's definitely leaking. Its hard to tell where from, maybe the intake to head, maybe head to block. Made sure the intake was torqued to spec and switched from a 16lb cap to a 7 lb cap, and went for a spirited test drive in the rain....
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0.010" off the heads shouldn't affect the intake mating should it? I'll take another look at the head bolt torque as soon as it stops raining. This is with flat heads, fresh gaskets, CLEAN surfaces. Maybe RTV squeezed up into the coolant port when I was setting on the intake and affected the seal? It's difficult to tell if it's leaking at the top and running down the head/block crack or if it's pushing out from said crack.