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When is it wise to upgrade your car and why

This is a very open-ended question, to which there's no right or wrong answer, depending on all the circumstances.
For many new car buyers, they like to upgrade every 3 years, or when the warranty expires so that they always the assurance of knowing their car should be totally reliable, and any repairs will be paid for by the manufacturer. Others may like to upgrade when a new model comes to market, while some don't like to buy the first of a new model, so wait until it's been around for a couple of years, so that in the event any teething problems, they've hopefully been ironed out.
Other factors to consider for used car owners are age and/or mileage. Many people choose to change their car just prior to a milestone mileage (such as 100,000km) which they feel is a psychological barrier to buyers.
Depending on the car, some cars may start to require expensive maintenance at a particular age/mileage, say 150,000km, so people choose to upgrade.
There are also times with older cars, where the value is such that a major failure (such as transmission for example) will cost more to fix than the value of the vehicle, so if they're driving a 200,000km car that only has a value of say $2k, they'll choose to sell rather than run the risk of a failure which may cost $3k.
So, as you can see, this is very dependent on the circumstances.