To be fair, plenty of people run aground, collide with other vessels or structures without having any technology on board.

I agree wholeheartedly that if technology is on board for the purpose of aiding to keep a vessel safe, that the users need to be very aware of its limitations and how to set it up correctly.
This is a difficult thing to achieve in a recreational setting, it's proving difficult to achieve 100% even in the commercial world.
The operator manual for our AIS clearly states how it can aid watch keeping but also why it cannot be replaced by the requirements of normal watch keeping (looking out the window etc) due to various reasons like not every vessel carrying AIS.
Our chart plotter always requires me to acknowledge the warning that it cannot be used as a primary means of navigation and does not replace paper charts when I turn it on.
Regarding personal ability to conduct a proper risk assessment in how to keep your vessel safe, yes personal issues and experience plays heavily in that space. But I think people also need to have a grasp how much is in the mix.
Having recently had the opportunity to watch a RAN patrol boat crew in action, it just highlights that although they have all the toys they still work hard to track contacts visually and don't rely on GPS to keep the vessel safe.
Their bridge routines may seem over the top to most recreational boaties, but it is a demonstration of just how busy it can be to meet your obligations under COLREGS.