I think your advice is objective. However, you do apply your opinions to others. Like car leases. You say they are universally a bad choice. But they can be good. I'm not a fan, but I wouldn't say car leases are all around bad. If someone said they leased a car, the response on a forum might be "that was stupid you'll overpay" but the response in person might be "oh cool, how do you like it?" Totally different. That's the internet syndrome at work.
And the gratification thing. Let's face it... Vacationing is all about aloof, unnecessary spending on self-gratification. There are ways to get everything cheaper in life. We just bought an appliance... Looked around for every deal possible until we got the max possible off. Most would just buy it -- should they be shamed if they go to a forum and talk about how much they love it? Whether that was time well spent would depend on your income and how busy you are, among other things. The OP in that other thread said his time was more valuable. At that point the discussion is over. No one can attest to his value of his time better than him, so it was financially a good buy.
What people tend to do is assume that everyone else values the same thing... optimizing. However most people really don't. To tell people they made a bad purchase for not optimizing in the way you would have, perhaps misses the mark because they weren't trying to -- they're just enjoying their vacation, and bought in, at a price they were good with. I bet a lot of people who pay more for their trips get more enjoyment out of them than some folks who perfectly optimize. That's what matters. When someone comes out here happy about their purchase and excited to go, the response will still be to dig in and see if they overpaid, since that is the voyeurism that the internet thrives on. Did they overpay, and can I point out how I could have done better. You see it all the time.
Another example is financing. You tend to be of the belief that one should never finance a
DVC purchase. I agree in principle, but still if someone wanted to finance it, and they worked it out so it works for them, then who am I to say they are making a bad decision? It's their money, and they want the vacations. I would welcome them to the club.
Another example is the dining plan. You can't enter the dining plan forum and talk about how you loved it and it was great without a flood of regulars ripping into you about how you overpaid. (shrug) It's unnecessary to be that way.