The cleaner itself, the Regultor Valve and the Flow Gauge will all be underwater when you test them. When you test the hose sections, try to keep as much of the sections out of the water as you can. Again, you're trying to locate how the air is getting into the pump, or if the pump is caveating and "creating" it's own air. Anything under water is not going to pull in any air through a leak.
If it's a leak, it's either in the vacuum system (and likely only the hose), the PVC pipe or elbows or unions or glue joints between the skimmer and the pump, any valves between the skimmer and the pump, any other component glued in in between the skimmer and the pump, or the pump itself. You'll need to test each of those things. We're starting with the components of the vacuum system.
If it's cavitation (which I don't know much about, but can guess) it'll be caused by some combination of pump size, pump speed and the amount of resistance being caused by everything in front of the pump (any or all of the things listed above). In order to test for cavitation, you need to maintain the resistance that was present when the problem occurred. For the most part, that means all the valves set as they were, and the vacuum in place (or the gauge standing in for the vacuum).
As you test each component, you're trying to get the pump to stall. You're starting from a point where everything possible has been removed from in front of the pump (which means every component of the vacuum system) and the pump is working fine (you've completed that step, right?), and then you're adding things back in, trying to get the pump to lose prime again. Each test of the vacuum system needs to simulate the suction resistance of the vacuum head. So either the flow gauge or the vacuum head should be included in each test. Since you cannot connect the vacuum head directly to the skimmer, or the regulator valve, then at least those two tests must be with the flow gauge standing in. If you want to test the entire hose all at once, you can, then if the pump loses prime, you'll need to go back and test each section by itself to find out which is leaking air (I know that contradicts my "one at a time" instructions, but this is just a variation of them, based on the fact that you're on your own here and probably need to get through this faster than I originally proposed. Up to you.).
As much as possible, for each of the tests, the flow should be maintained at the proper flow rate for the vacuum. So, again, that's why I suggested keeping the flow gauge in the circuit as much as you can. There's no point in testing when the flow rate is too high or too low.
If I was testing the hose sections for lengths of time like this, and had to observe the pump, I'd rig up something to hold the end of the hose (with either the gauge or vacuum attached), just under the surface. A length of pipe or 2x4, laying on the deck, with some sort of weight laying on it over the deck (a big rock, or some bricks, a sack of potatoes, a piece of furniture, whatever) and then I'd tie a piece of rope to the other end of the pipe/board and hang from that another weight to which the end of the hose is tied, the length of rope would be just long enough to keep the end of the hose just under the surface of the water. That way I could leave it like that for hours if need be, waiting for the pump to lose prime.
The wild card here is the filter, because it seems you've gotten mixed results depending on the state of the filter. I'm assuming the filter is still clean. Clean it if not before you test anything.