no way he has learned. if anything he is even more stubbord. there was a time that perhaps he was still interested and made moves, that didn't necessarily mean more money, i.e. trading for Roy Williams, which all the coaches on the team were against doing, but as a GM he didn't see he didn't fit the cowboys...and then trading for cooper, which was a good move because we had a bunch of #3 WRs playing and it was a weak point, proved that it was what we needed, went on winning streak and playoffs.
but when it comes to FA, he is stubbord. won't spend really, except his own and often its ROI related. Dak was top 5 in jersey sales and given Jerry and Cowboys are the only ones in the NFL pocketing Jersey sales, he loved it. same with CD and that's why Parsons will get resigned for whatever dollars because he was top three in Jersey sales one year. no way jerry lets that get away.
he has built in cost control with the cap. and as long as we are Pseudo competitive, he is happy. in fact he loves it more than sucking really bad or being really good.
does he want to win a superbowl? yes. of course. but its not his top priority nor his ego allows him to let it go to somebody else and do it and perhaps succeed which will make him look bad.