Sounds like you have a chip on your shoulder.
Maybe, just maybe, most of those you mention value their money more than you. Or maybe they are not as fortunate to have the abundance of extra money to spend on their planes as you. You must live in a much richer society than me, because all the people I know consider a $100 to be a good hunk of change. A trainer is more like $150 and those nice planes you mention are much more. So step down off your high horse and look at it from that perspective. Maybe they really do enjoy the hobby and do not want to risk crashing and having be grounded for months (maybe years) saving for a new plane.
Anyway, that is not even the point. The guy asked how much was too much to fly when he only has two flights on his trainer. It is commons sense for him not to fly in 15 to 25 mph winds at this point!
I totally disagree with you about if you don't fly in the wind when you are learning you are less likely to fly in the winds at all. This is insane

. It is so rediculous I don't even no why I am responding other than so the poster will not take your bad advice.
When I first started I wouldn't fly in hardly any wind. Now I will fly in just about any wind within reason. Now of course I am not going to go out when a front is coming through with 30 to 50 mph winds. But I am not afraid at all of the wind. I am not the greatest and landing exctly where I want when its really windy, but I am not afraid.
If I had a really really nice plane I would not be flying it in those conditions. Not that I would necessarily be afraid I just wouldn't want to risk all that money.
So I guess the moral of my post is, if you have tons of money to blow as Dusty here does, go for it, trash your plane and buy a new one.
If you value your money and have other things like bills that eat up a good portion of your money, then don't take the chance. Learn to fly confidently on calm days and then start flying in higher winds. It is the common sense and cheaper thing to do.
Good luck!
Wings