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I tend to check em if they don't 'feel' right... I'm quite fussy with me tyres I must admit... and after 4 years of driving the Caddy van, I got to the point where I could say - "the rear left's gone down a couple of pound.." and I'd be right... mind you it had suspension carved from stone, so any tyre pressure change was quite noticable...
If they feel ok, and the car's doing what you expect - ie no excessive wallowing in corners or slower/faster turn in than normal - even the action of the suspension can be affected, then I won't check em.. if something niggles that aint quite right - I'll check and adjust as necessary
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