I've been using ARB's deflator on several vehicles for ten years, with zero problems with valve cores. It's not a worry. You should have a good tire plug kit with you anyway, and the good ones will have spare cores just in case.
I'm a big fan of 100-percent duty cycle compressors. It just takes all the worry and wonder out of inflation. The Viair 400 is a fine unit, but a 33% duty cycle is pretty modest. In contrast to Vic I'd take the slightly slower 450P and its 100% duty cycle.
The ARB Twin is a brilliant compressor if you can afford it; I've never known an owner of one who was sorry he spent the money. A 100% duty cycle and astonishingly rapid filling. The portable kit is a beast, but extremely well-thought-out, and capable of running air tools if needed. Also, with the built-in tank, while you are moving around between tires the tank is still filling, which makes inflation even quicker.