I own a 2004 Itasca Meridian - similar to your Journey. Freightliner chassis, same CAT 330 engine as yours.
The air bags are rubber material, and will crack (and leak) with age. The best way to determine if they need replacement is by physical inspection and a leak check. After visually inspecting, spray a soapy water solution on them and check for leaks.
New bags are available, several places in the valley (truck shops to include Freightliner) can replace.
I replaced mine a couple months ago at the 140K mile, 17 year old mark.
If you replace the shocks at the same time, you will experience a great handling improvement.
To answer your last 2 questions, if one leaks badly, your engine compressor will attempt to keep it inflated. Can you drive with a blown bag? No. Those are air springs - no air, no spring and misalignment of your universal joints.
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