Hi Colin,
Glad you got them out.. and nice one for the update.
Having previously owned a motorcycle shop I have replaced countless head bearings.
Headstocks are generally only 2 types, with alloy frames the headstock is generally a cast and machined part and the seats for the upper and lower bearing cups have opposing ‘half moon’ recesses machined into them, usually but not always with the sharp edges rounded (usually the steel framed bikes that didn’t).
Steel framed bikes had the structural steering tube with, as you say, what is essentially a large washer welded in as the bearing seat while the frame is in the jig or the bearing seat was formed into the tube with enough room for a drift to get to the bearing. They also have the same recess’s cut into it.
The recess is generally about only 3mm ish less than the inner diameter of the cup, just enough for a decent drift to get a bite.
Looking down on the lower baring seat, a bit like this.. (sorry, quick jobbie in Paint!)
The upper one being the same.
We didn’t do a great deal of vintage bikes so I’m not really in any place to comment on their set up.
Then the budget imports began to arrive from the far east.. and it wasn’t long before I decided that for our own sanity and to prevent the easily foreseeable problems we would advise people on them but would not work on them as most of the time if you could get parts they were often worse than what you were taking off! Before we stopped, the headstocks on them would usually have just a plain ‘washer’ welded in as an after thought as the bearing seats (and rarely true to the headstock tube!) preventing any reasonable means of removing the bearing cups (basically a proper bodge).
Obviously I can not recommend that you file yours in a similar fashion for the reasons clearly stated above by J D 2 but it might be worth talking to your local bike shop for advise as they will see many differing set ups (ignore the newer sports bikes, they have adjustable insert bearing carriers to allow geometry changes to the rake and trail etc). They may well take a look and say go ahead or advise against it based on the set up.
Anyway, it’s a good excuse to have a wander to a bike shop for a cup of tea.. 🙂