Some people have a hard time practicing some do not. If you are fighting something that is the same over and over and is not a challenge, you should not learn from it. You shouldn't learn how to fight a dragon by killing mist wraiths.

If you are lazy, that is your problem. Gathering money or objects to barter with goes very easily for those who spent some time figuring it out.

Ranking is so not an issue for wilderness time. Over the course of your life, you may spend 100 hours (this number is high, but read on for the point) actually ranking, the rest of your time is doing other things. If your character lasts 500 hours, the wilderness percentage is not a factor. Not to mention that out of your ranking hours, you won't even spend half that time in a city. If you are an Outlander, you shouldn't be guild sitting to fit your other time anyway.

Forced hatred is a cabal dynamic regardless of the reason.

Your last sentence makes the most sense. But, look at it this way. If things weren't made more difficult, how would you grow? The reason why we go to first grade after kindergarten is because repeating kindergarten would get boring.