A story I always repeat when I hear about how (can we not beat around the bush?) a girl with oodles of dough is an advantage shidduch wise.
I know a guy who felt that way. He grew up in a modest household where both of his parents worked and just managed to pay for their childrens’ Torah education. He knew that there was no way he would survive in an American kollel and he ended up with a wonderful girl whose father was willing to support them for several years.
Well, it turns out that not all of the fathers money was Glatt Yosher and not even two months after the chasuna, all support was pulled out and the parents fled the country. The couple had to take on some serious debt and work multiple jobs to break even.
They are happily married now with several children, but I always think about how much more time he would have had to learn had he just decided before hand to plan things out a little and not just rely on his wifes’ familys’ support.