Hi Simon
After your high performance T/M's, any portable will feel lacking. It will probably be harder for you to judge the porty's vac performance than someone who uses one day in/day out.
After that, and presuming that your machines are running as per the manufacturers intentions, it does come down, as you stated, to AO v VO. On a twin vac machine, forgetting the " feel at the hose cuff" the performance at 15' I feel is superior with the VO (your set up) At 25' it's about equal and at longer lengths, the AO will take a marginal lead. But to be honest, there's not much in it unless you are running more than 50ft when the AO isn't as bad as the VO. Neither would be brilliant.
I don't know which tools you use for upholstery, but the CFR's, although cumbersome at first, are designed to be used with a single vac, so any twin vac machine would probably work better with this tool at longer hose lengths than a more conventional tool.
Just a final note, some twin vac VO machines I've come across are very sensitive to accurate assembly of the internal vac hoses and fittings. Just a slight error can have an enormous impact on performance. I've come across this with a colleague's Chemspec2000/Hydromist President.
Safe and happy cleaning

Ken