Andy,
If I have followed all of this correctly, the screw that is leaking is the primary case level indicator. Being that your bike is an A7, I am assuming you have a chain tensioner and the leaking screw is the one just forward of the tensioner. I also assume that the leaking oil is appearing on the outside of the primary cover, having leaked past the head of this screw. I suppose oil from within the crankcase can get pushed past the helicoil. It may not even require wet sumping, because the walls of the crankase are certainly fully soaked with oil when the engine is running. I think a little positve pressure within the crankcase would tend to push oil past most unsealed threads, not to mention loose ones. OK, fine, oil passes the threads and gets into the primary case. If its a lot, the level indicator screw is always submerged and more likely to leak if it is not well sealed beneath the head of the screw. Also, I assume there would be clutch problems. Even if it's not submerged, the level indicator screw needs to be well sealed. My parts book shows a fiber washer under the screwhead for the level indicator and (in the case of later A10's the drains screw). You should take a very close look, with magnification, at the shoulder where the washer should seal (assuming you are using a washer). That shoulder should be flat and not chipped or nicked or otherwise damaged. I can easily imaging someone (not you, of course) puttng a split lock washer under the screw heads and causing a gouge. If it is damaged, a touchup with a piloted counterbore would correct that condition.
I also had a thought that a messed up helicoil job (like, leaving the tab on at the bottom) could give a false indication of seating of the screw. therefore leaving it unseated and leaking. you did mention that is had a bad feel when trying to tighten.
There is another thing worth mentioning about primary case indicator screws. But first, let me say that I only know this because I read it in Chilton's BSA Repair Guide. On early pre-unit "A" models, the level indicator was where I said, but on later models BSA decided that a lower oil level in the primary was better, so they moved the hole behind the chain tensioner. Chilton recommends cutting away the inside of the cover at the rearward location similar to the forward location.
Well, Gents, thats it from me for now. Feel free to dig in and let me know if I have erred.
Richard