1. Yes, no vacuum breaker required. The fluid in the riser should acquire a final level equal to bottom id elevation of the last bit of horizontal pipe.
2. I also greatly favour no unnecessary holes in any tank, which is part of the reason I proposed my diagrams above.
You may of course get some air entrainment, however that may also be a more realistic approximation of final user conditions. Water devoid of all air is often not reality, but in any case, with a control valve in the discharge pipe holding backpressure on the filter, a vacuum in the discharge pipe downstream of that valve should not be of concern. (see next answer). Neither will siphoning extend through the valve to your test filter, so I see no problem with any configuration you want for the pipe actually going into the tank. You could even go over the tank rim and downturn, going all the way to the tank bottom with that pipe if you want. No stream to air exposure at all.
3. A back-pressure control valve set for your desired discharge pressure, or a differential pressure control valve on the discharge pipe going to the tank with a signl from a differential pressure transmitter across the test filter inlet and outlet thereby directly setting the pressure you want across the test filter.