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The upper level I don't know what the subfloor is, or if there even is a subfloor between the solid and beams.
You will have a subfloor UNLESS you have T&G boards running horizontally across the joists. I have seen this on second floor homes built from the late 19th century to pre- WW11.
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Question is: should the solid be ripped out before laying the new floor (risking finding only beams under the upper level floor) and adding a lot more work to the job, or will I be OK laying new over the old?
You can lay a new floor over the older existing floor IF you take the necessary steps. Re-nail or screw down any loose floor boards. Flatten the old floor to within manufacturer's recommendations. Lay the new floor at 45 to 90 degree angle to the old floor's direction OR lay 1/2" plywood underlayment over the old floor to be able to lay a new floor in the same direction. Check for height clearances before adding more flooring to the existing floors.
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And finally, if I can keep the old and add ply, presumably I still need a 'cushion' between the ply and the engineered?
It depends on what you are installing and how it is to be installed. If you are installing a floater, you will need a "cushion" as you call it. You could also skip the 1/2"underlayment. That underlayment is only needed if you are nailing or gluing. When nailing, we typically use #15 asphalt felt for 3/4" solid or thinner paper products like Aquabar for thinner nailed floors.