Those can seals almost always need replacing. I have rebuilt a number of DA's and RAM's and almost all were hard and crunchy plus you need to remove the cans to do a proper cleaning. By the way, they go BETWEEN the can and body, I have seen a number of them between the can and ring, it will leak if you put it there.. Without the proper tools these regs can be a bear to get apart, mainly because there is no good way to hold them without the tools.
As for holding pressure, it SHOULD, if it leaks down then there is a small leak somewhere. The 3 most common ones I have seen are the yoke to valve interface, it may have some small scratches or missing chrome, the nozzle is too loose or the hookah port is leaking. The nozzle is usually too loose due to not having the correct tools to hold it while tightening it but there is a second possible issue. If you use the old style pheonic seals, then they require a good bit of torque to get a good seal, conversely if you use the nylon ones Bryan includes in his kit, they require a lot less torque and if you torque them like the old type you can extrude them to the point they leak. The hookah port is often the problem, cleaning it and tightening it will usually fix it.
On all regs I rebuild, I assemble the body, connect it to a pony tank or a special HP hose I have then dunk it in a bucket of water to look for leaks. It's about a 50/50 shot that something will leak. Not bad, just a few bubbles and ok to dive but it won't hold pressure for long.
The single stage diaphragms will NOT work without a HPR. You must have the tabs for it to work on the original second stage. I suggest you consider changing them out. The old diaphragm ( unless it has been upgraded to a silicone one) will be stiff and hurt the performance of the reg, even new they were no where near as flexible as the silicone ones are. Another reason is the original second stage is a pain to set up properly. I can do it but I have a lot of experience at it, the HPR is much more plug and play and is very easy to set up.
If your reg has an old duckbill in it , odds are pretty good it is hard as a rock or a glob of goo.....or both. The best way to remove it is to soak it in denatured alcohol over night. The goo melts away and to the hard stuff turns to a soft jelly that is pretty easy to scrub out with an old tooth brush.
If you want tools for the DA or RAM and their Voit counterparts, I make a complete line of tools designed specifically for these regs. They will make your life a lot easier when servicing these regs . PM me if you would like a catalog.