Nowadays. I like to board the plane with just my mobile phone.
I will check in both my laptop and DSLR. I make sure my laptop is kept inside a bubble wrap and my DSLR and lenses in pouches. If they go missing, I will make a police report and claim from insurance. Then will go buy new toys.
Sometimes it is a pain to go through those security checks with so many gears. Many people are flouting the rules and bring more than what they can carry on. Sometimes you don't have space if you board the aircraft late.