My daily driver for charts is Luna Astrology. I use Astro Gold if I want to do a tri-wheel, but Luna is just so much easier to use that it spoiled me.
I use Astro-Seek.com if I want to do progressed composites, as neither of the above tools will do these. And there is always Astro.com of course.
I am currently studying with two astrology teachers:
Ari has a YouTube channel and a page collecting his free teachings. I like EA for its focus on karma and the evolutionary journey of the Soul across lifetimes. And I like Ari for his background in A Course in Miracles and the depth of knowledge he has about EA in particular.
I highly recommend her Archetypal Playground calls (free, you will get a link to all the prior recordings if you sign for that list). They go really in-depth into her own set of archetypes based on the twelve astrological themes (connecting Planet/Sign/House), tying them into myth and with a precision that is super useful. If you have any struggles in your life where you feel like some part of you takes over, or the same kinds of people keep showing up in your life causing you problems, I highly recommend diving into her work. Her Paradox School is also a great way to learn astrology if you feel overwhelmed by the prospect. Her focus is teaching human nature through the language of astrology, and it's very beginner-friendly.
People I watch regularly to learn and keep up on the AstroWeather: