[lldb/Docs] Add more details to the issues with custom Python installs on macOS

Although this issue is not specific to macOS, Python (in)compatibility
comes up quite often and we've been linking users to this page. This
just adds more details for this particular scenario.

Differential revision: https://reviews.llvm.org/D82507

lldb/docs/resources/caveats.rst

@@ -31,7 +31,41 @@ against Python comes with some constraints to be aware of.
     the one used to build and link LLDB.
 
 The previous considerations are especially important during development, but
-apply to binary distributions of LLDB as well. For example, the LLDB that comes
-with Xcode links against the Python 3 that's part of Xcode. Therefore you
-should always use the Python in Xcode (through ``xcrun python3`` or
-``/usr/bin/python3``) to import the lldb module or install packages.
+apply to binary distributions of LLDB as well.
+
+LLDB in Xcode on macOS
+``````````````````````
+
+Users of lldb in Xcode on macOS commonly run into these issues when they
+install Python, often unknowingly as a dependency pulled in by Homebrew or
+other package managers. The problem is the symlinks that get created in
+``/usr/local/bin``, which comes before ``/usr/bin`` in your path. You can use
+``which python3`` to check to what it resolves.
+
+To be sure you use the Python that matches with the lldb in Xcode use ``xcrun``
+or use the absolute path to the shims in ``/usr/bin``.
+
+::
+
+   $ xcrun python3
+   $ /usr/bin/python3
+
+Similarly, to install packages and be able to use them from within lldb, you'll
+need to install them with the matching ``pip3``.
+
+::
+
+   $ xcrun pip3
+   $ /usr/bin/pip3
+
+The same is true for Python 2. Although Python 2 comes with the operating
+system rather than Xcode, you can still use ``xcrun`` to launch the system
+variant.
+
+::
+
+   $ xcrun python
+   $ /usr/bin/python
+
+Keep in mind that Python 2 is deprecated and no longer maintained. Future
+versions of macOS will not include Python 2.7.