I think I may have an answer for you, Neonistic. The first Calypso regulators came out with this type of opening, and it was from the factory. The Conshelf must have come out just after that, before USD standardized on a HP thread type. What they had was a stem gauge in the HP port, as at that time the regulators did not use gauges on hoses much (a single hose regulator was a "single" hose regulator). That stem gauge was equipped with a washer that fit between the gauge and the O-ring. So, get a stainless steel washer with the opening for the fitting, and put an O-ring behind it. I know, as I have two Calypso regulators, and one still has the original stem gauge on it, with this type of opening.
Or, go to a LDS and ask to see all their old HP & LP plugs. Look for a weird one with both a washer and a metal protrusion that has a opening (for a stem) in it. This is the original stem gauge that went into that kind of opening. Also, I'll look and see if I have an old one in my dive tool box--don't think so, but it's worth a look. Maybe one of the vintage divers has one laying around too.
One of these two methods should allow you to use the current gauge you have with this opening--fitting a washer to fit between the O-ring and the body of the fitting to give you a sealing surface on both sides. I'll try to get a photo later, but I've had to redo my computer after a crash and don't have all the software set up yet. In any case, I'd do this before trying anything drastic like milling the regulator. I have a pressure gauge on my other Calypso, and I believe I did that to it with the washer.
SeaRat