How long does a Linux install last for you on average, before you completely re-install (on your daily driver machine)?

Lucky, maybe, sometimes. In reality it was a bit of experience and following the Debian way. Of course you cannot update blindly, sid can and will bite. The art is to let the bugs bite the others first.
Debian sid is not for beginners nor is Arch but both are perfectly usable almost indefinitely on one machine until the hardware dies without any reinstall.

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My experience running every interim of Ubuntu since 8.04 has been no, any performance change I have seen isn’t the result of cumulative updates. Some interims are faster and some were slower but my main concern was making sure I didn’t miss something useful in any new paradigm presented. That disk has been cloned 4 times and upgraded through 3 different laptops from 2 manufacturers with never a minute of downtime.