My boots were really worn when I bought the plane, but I nursed a number of extra years out of them with patching. In fact I got 3 or 4 more years than BootsEdge said I could get (they said I need to give up and replace them). I got good patch jobs done and they kept inflating firmly and doing their job.
Finally they reached the point where there just wasn't enough material in various places, and the leaks were too great. So I gave up this past year and replaced them.
My mechanics who nursed them along during that time did a simple soap bubble test with a small controlled air flow into the line when they were looking for leaks.
BTW, you really affect boot life significantly depending on whether an aircraft is hangared or not. OTOH there's always the argument of which costs more - the hangar charges or the repairs/replacements. But in the case of boots I personally believe hangaring is more critical than other things.
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