How do you decide when to upgrade your gear?

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How did you learn when your photography skills were holding you back and when your technology (say sensor resolution or autofocus speed for wildlife) were holding you back?

It's gonna sound strange but... with enough experience you'll know when you know that it's time for an upgrade.

Basically, it's gonna be that moment when you have an idea of an image or you encounter a situation that your gear can't capture it the way you want it, no matter how much you try to use your skills.

Also, one thing I learned is that renting now and then some new gear can be an eye opening experience. For example, ages ago, I was shooting with a 300mm f4 and was happy with what I got from it. Then I rented a Sigma 150-600mm C and was amazed at the new possibilities it opened up.
Ditto after shooting with an A9 and it's "blackout free" EVF.

Nowadays, even the cheaper cars are more reliable and if they're more expensive and more complicated to repair, at least they don't NEED repairing as often.

I think the automobile had a golden age in the 2000s up to around 2012, when cars where advanced enough to be reliable and comfortable but not complicated enough to have all sorts of things to break down. These days there is too much technology in a car and most of it is done by the cheapest bidder...

I took my car in for service last month at the dealership (one of the biggest brands in the EU) and I was talking to a service rep about buying a new SUV. His advice: avoid the newer models as they are full of electric gremlins and go for an older platform.
 
I think the automobile had a golden age in the 2000s up to around 2012, when cars where advanced enough to be reliable and comfortable but not complicated enough to have all sorts of things to break down. These days there is too much technology in a car and most of it is done by the cheapest bidder...

I took my car in for service last month at the dealership (one of the biggest brands in the EU) and I was talking to a service rep about buying a new SUV. His advice: avoid the newer models as they are full of electric gremlins and go for an older platform.

I don't know about the EU, but we've bought a few new cars in the last four years in our family and that hasn't been our experience. Only issues I had were taken care of quickly and never reoccurred.
 
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