The "dash air" in older Class A gas coaches was really a mess. I say "gas" because I know about them, and not much about diesel pushers. Both share the issue that the chassis supplier send a bare chassis and the coach builder adds the Dash Air among many other things. Years ago, the Class A Dash Air was cobbed together out of whatever the builder could find, could get a price on, or their suppliers could provide on demand. No quality control, very likely not even a knowlege of what the parts were for repair time.
I THINK it's gotten better. A/C provided by chassis supplier, or at least a motorhome unit bought as a unit by the builder. I also have a lot of confidence in Winnebago as being one of the better builders.
This could be as little as a wire off, connector unplugged, etc.
A "static" pressure test tells you very little about whether you have adequate refrigerant in the system. It's the nature of refrigerant to expand to a certain pressure at a certain temperature regardless of quantity in the system. Say it calls for 36 ounces of R134A. From a Chart, R134A at 85*F will show a static (system not running) pressure of 95.3 PSI. It will show that 95 PSI full at 36 ounces or nearly empty at 6 ounces. But turn it on and it sure won't cool at 6 ounces! In fact, if it's that low a low pressure cutoff switch won't allow the compressor to even run. So YES it could have leaked down.
If your dealer's good, they'll find it and fix it. If they're good and can't they'll arrange it to go to somebody who can.
On the other hand, a good shade tree mechanic might just find there's a wire off.
But it needs to be looked at. And I'll wager you'll get the cold air you want when it's corrected. I drove a used 30-ft Winnie Sightseer in FL on a hot day and it cooled fine.