This is expected behavior. What you can do is to either:
1. Extrude continuous face loop (like left option in your screenshot), then delete unnecessary faces and fill the hole; still won't work on extreme extrusions for less than right angles;
2. (preferred) Extrude for how far needed, then do manual "untangling" by simply moving intersecting parts.
It is rather feasible that you would predict what program will do, than program predicts what's on your mind next.. at least, not for current state of AI. 😉
,,,_°(O__O)°_,,,
Maya2019.1 @ Windows10 & GeForce GTX1080Ti
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