I have a very different model of financial planning than you do. I view spending money in exchange for time now as equivalent to spending future free time in exchange for present free time, as it increases the amount of time I will need to work until I can retire passively off of investment income. For me, retirement isn't some far out, dubious prospect, it's a very real thing that I have created a specific budgetary goal/timeline for. I can't generally trade free time for money in arbitrary quantities. I'm okay with trading time now for time later, because I don't think all free time should be valued equally. Free hours are worth more if I have more of them consecutively, don't have to go to work the next day, and when friends are available.
I think the value of free hours in general is much greater when I can elect to have a whole week of free hours, even if I don't truly stop working. Once one has retirement saved for, they truly can set their own hours, and if someone asks them to do otherwise, they retain the option to tell them to screw off. Not having a Sword of Damocles hanging over me is something I value highly.
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Regarding preference utilitarianism, why can't the negative utility of not having a preference fulfilled be modelled with average or total utilitarianism? That is, aren't there some actions that create so much utility that they could overcome the negative utility of one's preference not being honored? I don't see why preference fulfillment should be first class next to pleasure and pain.
Sorry if this is off-topic, that was just my first reaction to reading this.