In the case of housing, it is generally very not normal for resale to be less than purchase price. Sure, there are exceptions to that: market downturns happen, and sometimes regional issues (like the one big employer leaving town) can cause that. But in general, no, it's normal for the resale value of a home to be higher than when you purchased it.

That's dumb. But that's the reality we live in.

You are correct! These are indeed the general trends and there are those exceptions. Some win, some lose and there are general trends in play.

This is the market. So I maintain that guaranteeing outcomes is craziness.

Should something as vital as housing be a market commodity? That's a whole different conversation.