This is where a test flight really pays off before buying. A leaky airframe will show itself through a lower differential cabin pressure. The max is 3.35 psi. My current P337 achieves it no problem. The previous one did as well. Not so an aircraft I looked at that only went up to 1.7 or so.
The pressurization system is actually pretty simple and mainly maintenance free. I just did a major annual and while there was a lot to do to get the aircraft up to the standard I wanted it at, pressurization was not an issue.
And it is a major plus when going places. It all depends on how you want to use your airplane.
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