From my experience that rolling off thing is not true of the vacuum two speed in the vintage of Chevy truck that you have. As you have confirmed it takes vacuum to shift to hi or lo as noted by your test of the lines and the vacuum swapping from one to the other. I have been around a handful of Chevy trucks with vacuum two speed axles from the sixties and never heard of this being an issue. This may have been true of an axle with a different design where vacuum made the shift to hi or lo, but a spring returned it to the opposite speed. As far as having a good emergency brake if there was a disconnect in the rear axle it would not help anyway because the emergency brake on those trucks is on the back of the transmission and locks the driveshaft from turning. Wheel chocks would work in any case.
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Today's Featured Article - Product Review: Black Tire Paint - by Staff. I have been fortunate in that two of my tractors have had rear tires that were in great shape when I bought the tractor. My model "H" even had the old style fronts with plenty of tread. My "L" fronts were mismatched Sears Guardsman snow tires, which I promptly tossed. Well, although these tires were in good shape as far as tread was concerned, they looked real sad. All were flat, but new tubes fixed that. In addition to years and years of scuffing and fading, they had paint splattered on
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