Well, Its not a good idea to re-ring a aircooled for two reasons in your case. I won`t get too technical.
#1- Piston wear. The ring lands will wear enough where the new piston rings will be "sloppy"(up and down) and you run a chance that the piston will break in half in the ring groove do to the drag of the new ring. I have seen this time and time again.
#2- 40pds of cold oil press ? What is the press. hot and at an Idle ? If you are showing somewhere around 5-15 pds hot , This might , I said might , indicate a issue with main/rod brg. wear. Then you come along with new rings or a piston/jug set. The drag of all this new stuff over the worn out bottom end, well I think you get the picture. Im not saying this the case with you, but if you have no history on the engine,I would wonder if I would take the chance. Your call. You might get away with it. I have bult some "off the floor engines" for my junkers over the years. sometimes I got lucky.
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