We've seen both ends of the spectrum, from aircraft owners who do minimal training and fly questionable aircraft to those who invest heavily in training, equipment, and maintenance.  Naturally, economics have some role to play in how an aircraft owner treats their training and equipment, but most of the time the primary driver is the their philosophy and attitude.

Take, for example, the owner who does little training but invests heavily in every new gizmo that comes on the market.  This person tends to convince themselves that technology will keep them safe.  On the other hand, there are those who are frugal investors in new technology but will spend the time and money necessary to ensure their skills, decision-making, and knowledge of their craft are always up to par.  Which pilot would you rather fly with?

Here's my two cents.  If you have the means -- and ability -- to equip your aircraft with (and properly use) the latest equipment and take advantage of excellent training opportunities, then you should absolutely do so.  But, if you need to make a tradeoff between a rapidly depreciating piece of avionic equipment and the chance to make yourself a better pilot, my money is on training...every time.