What exactly do you mean by a "Wheel error"? Show me a reproducer and a proper error message and I'll be happy to help to the best of my ability.
By and large, the reason pip fails to install a package is because doing so requires building non-Python code locally, following instructions included in the package. Only in rare cases are there problems due to dependency conflicts, and these are usually resolved by creating a separate environment for the thing you're trying to install — which you should generally be doing anyway. In the remaining cases where two packages simply can't co-exist, this is fundamentally Python's fault, not the installer's: module imports are cached, and quite a lot of code depends on the singleton nature of modules for correctness, so you really can't safely load up two versions of a dependency in the same process, even if you hacked around the import system (which is absolutely doable!) to enable it.
As for finding significant whitespace (meaning indentation used to indicate code structure; it's not significant in other places) hard to read, I'm genuinely at a loss to understand how. Python has types; what it lacks is manifest typing, and there are many languages like this (including Haskell, whose advocates are famous for explaining how much more "typed" their language is than everyone else's). And Python has a REPL, the -i switch, and a built-in debugger in the standard library, on top of not requiring the user to do the kinds of things that most often need debugging (i.e. memory management). How can it be called hard to debug?