Just a couple of points that spring to mind
There are kegs other than 5 US Gallon Cornes, there are lots of the old Australian 23L (5 Imp Gal) kegs kicking around, here are a couple on
eBay, should make for much better batch sizes.
PRV's cant leak gas in, well unless they are stuffed, they are basically a one way valve with a spring holding them down.
I to would be very concerned about O2 ingress, not just HSA but if you are no-chilling in the keg - plain straight old fashioned oxidisation - the beer wont be better for exposure to oxygen for any length of time.
Both poppets can let air in as vacuum forms, for air to travel in through the liquid the vacuum would have to be the same as the wet height of the dip-tube and the density of the wort according to P=ρgh (ρ being density, g gravity, h height). Just on my fingers about -6 to -7 kPa (about -1 psi for the luddites) so more than doable if the gas poppet was a bit sticky.
I think the perfect solution would be a CO2 and cask aspirator, it just lets in a vacuum relieving amount gas.
I have a friend who was doing this, brewing here in Newcastle, putting the wort into a 45L keg (the old Australian type with a hatch and poppets like a corny), pressurising with CO2 as the wort cooled, then fitting a HEPA filter to the gas post for the drive over the range to Tamworth,
The beer was never as good as that which was taken home in cubes, we put it down to oxidisation from air getting in and out from the altitude change, he has gone back to using cubes.
Mark