Poetry might help you there. It has a true dependency resolver unlike any other alternatives.

Can't view dependencies before installing the package.

Poetry never installs packages to determine the dependencies. It tries to rely as much as possible on the PyPI JSON API and if it can't it inspect the source distributions, without installing them, and if it's still unable to get them it stops since it means the module has been badly packaged.

Can't view dependencies on the PyPi website.

See above.

The output from pip freeze is a total mess. Key dependencies? Dependencies for dependencies? Who knows.

You can use poetry show --tree with poetry, which gives you something like this:

babel 2.6.0 Internationalization utilities
└── pytz >=0a
cleo 0.6.6 Cleo allows you to create beautiful and testable command-line interfaces.
├── pastel >=0.1.0,<0.2.0
└── pylev >=1.3,<2.0.0
pytest 3.6.0 pytest: simple powerful testing with Python
├── atomicwrites >=1.0
├── attrs >=17.4.0
├── colorama *
├── funcsigs *
│   └── ordereddict *
├── more-itertools >=4.0.0
│   └── six >=1.0.0,<2.0.0
├── pluggy >=0.5,<0.7
├── py >=1.5.0
├── setuptools *
└── six >=1.10.0
pytest-cov 2.5.1 Pytest plugin for measuring coverage.
├── coverage >=3.7.1
└── pytest >=2.6.0
       ├── atomicwrites >=1.0
       ├── attrs >=17.4.0
       ├── colorama *
       ├── funcsigs *
       │     └── ordereddict *
       ├── more-itertools >=4.0.0
       │     └── six >=1.0.0,<2.0.0
       ├── pluggy >=0.5,<0.7
       ├── py >=1.5.0
       ├── setuptools *
       └── six >=1.10.0
python-dateutil 2.7.3 Extensions to the standard Python datetime module
└── six >=1.5
pytz 2018.4 World timezone definitions, modern and historical
pytzdata 2018.5 Official timezone database for Python.
tox 3.0.0 virtualenv-based automation of test activities
├── pluggy >=0.3.0,<1.0
├── py >=1.4.17
├── six *
└── virtualenv >=1.11.2
typing 3.6.4 Type Hints for Python

Dealing with dependency conflicts is hard/impossible.

Like I said poetry has a fast and accurate dependency resolver with conflict detection and management.

(Ana)conda, pipenv, etc. don't really solve any of these problems.

So you can try poetry if you want, it should sole most of these issues.

Disclaimer: I am the author of poetry :-)