Hey Bob, you said regarding your son:
"He now is considering getting new shoes, but still, insists on spending the least amount of money. I think I'd at least like to convince him that good shoes are one of the most important investments you can make."
How will you convince him that he is worth good shoes if you don't think you are? I empathize with your feelings though, my ex was very frivolous with money, and it made me feel like i always had to be the one to say no. Very imbalanced. You buying yourself decent shoes for work when you are on your feet all day is valid, and doesn't mean you are frivolous or irresponsible with money or selfish. I think you should be able to get some good ones for $100 tho, i'd be wary of the $300 ones! Take care of yourself, you deserve it.