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I haven't found the limit either. My 2018 iPad Pro renews monthly for about 8 bucks. the thing I often wonder, is that at some point you'd think apple would stop letting me cover an older iPad, because in the event of a device replacement need, they might have to upgrade me.
 
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Other than the link you showed, I can’t find a real answer to that either. Considering I still have and use a 2012 Mac mini and a 2014 MacBook Pro 15”, they can last a long time, and usually do. So it would be nice to get AppleCare+ beyond 3 years if the device is still valuable enough to justify it. Apple is really bad about being cryptic about things, so it is tough to find any answers. I just ordered a MacBook Air M1 with 8x8 cores, 16GB RAM, and 1TB SSD, so I will definitely get the 3 year plan, but it might not be worth a renewal after 3 years depending on what the coverage would be and how much value it still has. But at this point I have no clue if I can even get coverage after 3 years.
 
Apple offered 4 and 5 year AppleCare at a significant premium. This was for corporate customers I believe. I would definitely renew annually given the option.
 
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