Personally I don't think there is anything wrong with this debate. my analysis is that we have 3 types of camps here
1) Camp 1 - that does not see anything wrong with - kufuta jasho after a hard day of work. they ask - nani alikuwa anatafutiwa anyway? Kujilipa
2) Camp 2 - that has book knowledge of how to spend money... large amounts of money wisely. discussing how to spend money here are actually regurgitating principles they have learnt but not tested.
3) Camp 3 - a subset of Camp 1 that think everyone in Camp 2 is a hater! has Kiwaru! A school of thought where they are an important part of the universe and there are roving green eyes looking at their every move. Most of them being imaginary. Sorry, you are not that important.

I personally think I am in Camp 2 - one that believes in delaying gratification and getting pushing the celebration of their success perpetually into the future. But i think I am also not fooled into thinking it's easy! coming across cash will test you proper! just because you know it's supposed to be done does not make it easy to do! SIMPLE things are not to be confused with EASY! that is where culture comes in. what is your social currency? - what is valued by yourself and your circle of friends. <-- culture plays a big role in defining this. That is why I asked you to examine the communities who do well. As part of their culture they sort this out. They build character in the midst of wealth. Most (not I said Most not All) sports people come from poor backgrounds and their talent puts them where their character cannot uphold them. Sometimes you have really wealthy people who seem to have it honed. Akina steve jobs - they were net successful but grew up poor(ish). Utaona private jet or yule jamaa wa Oracle! if you look at the jewish lot. Akina Zuckerberg, Larry Page e.t.c. they are happy to ride economy. Gates used to do coach as well. Mimi? hehehe... sitaRide coach nikipata nafasi.
It's true that old money does not do these things unless they want to impress their friends who are not in old money circles. I guess it depends on what your social currency is it's possible that people who have grown without worries don't feel obliged to spend especially if they are surrounded by people who also grew up in those circles. if they are striving to impress (social currency as well) everyone - they put up photos of their toys on social networks. It's the same for people who put their clothes they have, cars they have, food they are eating, places they have eaten been to, every seemingly clever/witty/hiraous thing that comes to mind , people who feel obliged to tell us where they have traveled to (duniani) e.t.c. No one is perfect ( think i am in the last two)
But hey - these are just my opinions. but i think money (and power) magnifies attributes of an individual.