I've been dealing with Apple computer gear for a long time, as have my friends and family.
Here is a list of the old gear that me and/or my friends have in active service. Note that this gear is in real service, and isn't treated as museum pieces or as part of a retro-computing hobby.
- 2008: Apple Airport Express, draft-N, first generation
- 2009: Apple MacBook, late 2009 (utility use only)
- 2010: Apple iPod nano, 6th generation
- 2013: Apple Airport Extreme AC
- 2015: Apple TV HD (4th generation)
The big winner here is the Airport Express, which is modern enough to do its job, and it just keeps on going. The device that my friend runs has been in operation for more than 125000 hours. It received its most recent firmware update on 28 August 2018, 10+ years after its initial release. In terms of security: it has no open, unpatched CVE vulnerability reports.
Many generations of other routers have come and go while this one keeps going.