First question, what did you have in the radiator? If there was an antifreeze mix and you're getting plain water out of the crankcase, then it will be a matter of condensation if it's justa little water, or rainwater if a more significant amount.
On the flip side if you had plain water in the radiator (or if you had an antifreeze mix and that's what you're finding in the crankcase) then there's more looking around to do. Since you had the head off, I'd assume the tops of the pistons were dry. Now that it's back on, go ahead and refill, and start looking arooud for leaks. Easiest and first place to look is by taking off the pan. If it's seeping around the bottoms of the sleeves, then you can suspect the o-rings. If coming down out of the oil gallery you can suspect the head, the crankcase or the gasket.
As far as pressurizing your cooling sytem to check it, you'd have to rig a cap to take air pressure and find a way to block your overflow if you do to that the air doesn't just run out without building pressure.
If you don't find any leaks, I'd refill and giver a few good warm runs and keep an eye on it. And don't forget to retorque your head gasket.
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