I deleted my original response because I realized that I could make this real simple.
If you look at the head curve of a 3/4 HP two speed pump, you will notice that at 0 GPM it reaches a maximum head of about 20 feet or so. This means that with a pipe 20 ft in the air, no water will come out of the top, 0 GPM. There is a good chance you will burn up the pump in the process too.
If the vacuum valve requires 2 PSI to close, then the maximum head loss possible is 15 feet (20-5). If your roof is lower than 15 ft, you may have a chance at closing the vacuum valve. If not, you are out of luck. Its that simple.
Even if the valve does close, you need quite a bit of flow to push the air downwards to completely prime the pipe. So in reality, your are limited by much less than 15 ft.
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