No doubt Ben, but there is a fine line in these scenarios. It is the line of being too conservative vs. living once. No return on investment, and remember, scenarios like this require a full investment to be made at once in the example you gave, can compare to memories made with family and friends vs. watching numbers grown in an account you may never live to see or use.
1. People need reliable transportation for work and for pleasure.
2. The cost of pleasure differs from person to person/family to family and neither is right or wrong.
My wife and I made certain choices when it came to pleasure spending. Instead of spending a couple thousand each year on beach vacations, that $ was put into trucks & campers. Did it cost more than yearly beach vacations, absolutely! But, and a big but for us is you can't put a pricetag on memories made with your children when young and we want to be able to do that more than 1x/year.
Being able to hook up and go whenever the urge hits is a great feeling and having confidence in the equipment to do so is a small price to pay.
Unfortunately, $100K in a new 5th wheel and truck combo is the low end these days. I don't fault you one bit (ain't none of my or anyone else's damn business what you do with your $) if you go that route. I'm just saying don't make rash decisions on such large purchases.