I've not really had too many leaks from the water jacket covers, even from motors that have sat for decades. If you ever take them off, you'll see that crud tends to accumulate around the edges and crust over.
But that said, everything else about the cooling system needs to probably be freshened up, including doing a flush. The water pump may have seized and the hose going from the block to the pump dry rotted (doesn't help they also bake from their location). The whole process to overhaul the cooling system is only a couple hours once you have the parts. Rebuilding the pump isn't that much longer (or just get a rebuilt one) for the peace of mind.
In my case, I went through my Roundside with an eye towards getting everything freed up and belts / hoses redone, only to find it leaked oil from like 3 different places once I got it going after sitting for so long (15+ years). You probably know this, but heat and circulation will loosen everything up, so it's hard to predict just exactly where leaks will happen. When I did an oil change, it was basically black goo that I let drain overnight, so I did another change about 250 miles later and it looked way better.
The good news about all this is, Crosleys are easy to work on and it's amazing what you can get done in only a short time. The vendors can assemble you a kit and will have more insight than what's spelled out even in the manual.
Good luck and see you at the Nationals!