It's a bit difficult on a 5000 due to the way the pan is attached. However, you need to remove the pan. Use a cooling system pressure tester to pump the system up to normal pressure and observe the underside of the engine for leaks.
 
(quoted from post at 22:09:55 04/23/11) Changed head gasket on a 5000 ford 256 engine still leaks a considerable amount water in oil any ideas?

Did you also have the flatness of the block and head checked and corrected?

For some of us, it's just now starting to get warm enough to mess about, is this leak new this spring? Could it be ice damage that cracked the block or head?
 
Fords rarely blow headgaskets,will bet you have a hole in a cylinder wall.It will have to be bored and sleeved. Sleeve all of them while it is out. Around here it costs about 125.00 a cylinder.I have done dozens of them over the years. I just did a 401. Changing anti-freeze and coolant conditioner would have prevented this.
 
I've found in every instance of bad head gaskets on mine that they charge the cooling system with combustion gases. Never had one drop coolant to the pan; at least not yet.
Since yours is losing coolant to the pan I would wager on a pinholed block... You're going to need to drop the pan and put some pressure above and see where the leak is at.

Rod
 
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