OPP, I think it's about more than just the money. I don't know this guy well enough to really know how well off he is. He did play at the big league level for more than a few years. Heck, he even has a ring from one magical year. I think his dilemna is more from the standpoint of what the heck does a guy do when he's done with baseball?
Even if he's fine financially, when you're only in your 40's, its kinda hard to just sit back and play full time house husband, I would think. I think its great for the guys who are able to get jobs in the game, either coaching or scouting; but that sure doesn't take care of the number of players who leave the game and don't have the skills to have multiple career options, or the money to do nothing if they so choose.
The region I live in has produced a large number of professional players, many major leaguers. Of those players, most were taken either out of high school, or more commonly, out of Jr. College. I wonder how many of them have real life career skills. I do remember an acquiantance, back in the 80's, that was on a MLB 40 man roster. This guy drove a milk delivery truck in the off-season to make ends meet. Nothing wrong with being a milk man at all, but it was kind of a surprised to see a guy doing this, who played major league ball at the same time.