You seem to think that pilot Bob has to have a sideslip at some point in the pattern, because he has to make 90 degree turns in the air, and somehow also has to follow the groundtrack with 90 degree turns.
However, that's not the case (at least not if Bob is anything resembling a good pilot).
If he wants to follow a groundtrack with 90 degree angles, he has to adjust his heading, and the path he flies in the air looks something like this: (the wind is coming from the right)
At no point in this pattern is he in a sideslip, or doing something weird. You could do this pattern as well when there's no wind at all, the only difference is that in that case it follows an usual groundtrack. There's just one reason to follow this weird pattern today: because with the wind acting on it, this pattern will be bent into a nice rectangular groundtrack, which is what Bob wants.
And there's no real danger here, except when Bob does stupid things (like flying close to a stall and then entering a turn). The only danger you could argue there is that two of his turns are somewhat longer than the usual 90 degrees.
Related, you seem to think that crabbing is somehow difficult or dangerous. But whether you are crabbing or not makes no difference at all as long as you're not close to the ground. Only landing with a crab is difficult, because you have turn the nose (de-crab) or your landing gear will push you the wrong way.
In a sense, a plane flying due north while over the equator is crabbing heavily, because its nose points due north while its "groundtrack" as seen from space is east-northeast. Because it's moving along the Earth's rotation of ~1,000 mph. But does this matter? No, not as long as you don't want to interact with any satellites or other things outside the Earth's atmosphere.