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Princetons and other "cleaner" amps are less forgiving, and it only really bugs me when intonation on the guitar is off! Otherwise, I often REALLY need that "unforgiving" clarity for some stuff I record.
As far as "less forgiving" - you may get a backlassh by some of the more snobby guys here, so be careful :)
The Montogomery Ward/Airline is likely getting you about 25 watts with a very tweed topology. So the wattage of this compared to your Prince isn't really fair as the Airline will be much warmer and edgier... regardless, I'd still stick with the "low-watt's low-watt" idea of the Airline and go for an earlier 2x6L6 tweed style amp... some folks make those or offer kits...
Perhaps a Lil Dawg 6L6 modded 5E3, but again, the early tweed circuits got dirty/warm all over the place, so see if you can talk to a 6L6/5E3 owner before committing.
Sounds like you want the right mix of warmth (more forgiving), with the right amount of headroom (to still get you some cleans at gigging volumes)... may be hard to pull off.
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