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saddlesores...
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His diagnosis was that I was using rims that were too light and too flexible (and used). Another issue is the general deterioration of roads around here and in at least one instance, hitting a bump hard enough was enough to total a wheel. He suggested a stronger and new rim (such as GP4's if I wanted tubular) and when the 40 holes popped up they seemed the correct way to go. In retrospect, a good set of used Tandem rims might have been cheaper.
As for tubulars, it is a preference. Probably tubeless would be a smarter way to go but I'm almost 60 so let's blame it on an old man who is set in his ways
So far your investment is for two rims, maybe you only need one hub? To get a complete set of wheels, a set of tandem wheels may be the cheapest at this point. But if part of the problem is rough roads, instead of trying to make a skinny high pressure tire work on a rough road, I would give in and use a wider clincher if your frame will take a wider one. For one thing, that would be more comfortable for you the rider.
Whether it be tubeless or not, I call that personal preference too, I am 68 and I am sticking to tubes, set in my ways. I have never had a snake bite flat, but I rarely ride on anything narrower than 32mm. My road bike is 28mm but that does not get many miles.