What to read?

Reddit has the information already there, people just don't look for it, and then ask, and people refer them to the sidebar. You couldn't go too wrong with their book list.

I personally would not put any Chogyam Trungpa on the list because he did not exemplify the discipline. I do think about his idea of idiot compassion, and the critique of materialism is OK. I hope someone can come along and update that book.

I stumbled on Jack Kornfield, Pema Chodron, Lama Surya Das, Charlotte Joko Beck, Ayya Khema, and Thich Nhat Hanh. Those were not bad writers, and I really think what you stumble upon will be good enough. The process of finding books should be one you own. There's enough information out there. If you don't have good book reading habits and don't have book lists around you, then putting it on other people isn't really developing the habit yourself. Take responsibility. 

Even so here is my first thoughts:

Breath By Breath. There are many good books about anapanasati, but I think this is a good first book on it. Already I'm showing my bias towards meditation. The Buddha became enlightened through many circumstances, but one of them was that he was meditating. 

You should start meditating on the breath, with this as a guide about the full eventual possibilities. Human face to face support in meditation is very important. It's easy to skitter off. Take a class first and then if you think you're going to go in this direction, then read this one. Already you're going to be connected to a sangha by taking a meditation class. Maybe your entry is by a talk. Or going to a drop in. Maybe you met with someone. Maybe you attended a zoom meeting. 

I like to have a deep ancient book to pair with modern interpretations. So I would also recommend reading the Dhammapada, then the Udana, then the Saṃyutta Nikāya, then Dīgha Nikāya, then Majjhima Nikāya.  You could linger on those those books for the rest of your life. 

The Mahayana sutras, Perfection of Wisdom and Pure Land sutras are also amazing. There is a book about Buddhist literature, The Eternal Legacy by Sangharakshita. There are a million books about Buddhist history but every book make a choice about what to focus on. You have to make a choice about what you are interested in. You have to pick a sect that will also narrow your choices.

Tuning in and trying to change will help you to realize you need to work on yourself. That is when I would next read Radical Acceptance by Tara Brach. I think that the pairing of modern psychology can really lay the groundwork for sorting yourself out, and cultivating a growing mentality. There are people who think that's watered down, or bringing in something that isn't traditionally Buddhism into Buddhism. The fantasy that we don't have modern ideas, and can just live off ancient ideas 2,500 years ago is appealing to me. Cuts down on a lot of reading to eliminate the enlightenment and modern psychology.

To further the positive mentality I would then work on the Brahma Viharas. Christine Feldman's Boundless Heart hasn't been surpassed yet to my knowledge, I hope to find more books on this amazing meditation.

I like pairing meditation technique with Dharma and history. There's a natural synergy to that pairing in reading. Whether it's Pali Canon, or Mahayana sutras, or modern histories. There's a lot of directions you could go here, and in a way it depends on your sect. At this point you should be engaged in a sangha, and they should be telling you what to consider reading. 

Many people on r/Buddhism disparage Triratna and NKT, but if I'm really honest, the most people I've met who were Buddhists were from these sanghas. What does it mean to be popular but scored by traditionalist Buddhists who want you to go to an established sangha? You could almost say that it takes a pervert like Chogyam Trungpa to bring Buddhism to America. You could almost say you need a uncharismatic victorian to bring Buddhism to England in Sangharakshita. You could almost say you need a weird egomaniac like Kelsang Gyatso to imagine we needed a new Tibetan order. I actually like his books. Hannah founded many sanghas, and her husband isn't the one who did it, but took over her sanghas when she died. Ambedkar converted to Buddhism, encouraging the Dalits to do so too, and then he died in 1956. Nobody as dynamic has harnessed his people. Daniel Ingram has broken the taboo of saying you're enlightened. There are plenty of figures who open up the Dharma to people, but then are heavily criticized for being imperfect and not traditional. IMS has a kind of heresy to deny the lay monk split. 

You can't recommend books without stepping into this controversy. 

I would almost say you need some kind of charismatic person to transmit the Dharma to the west. We like our hucksters, snake oil salesmen. Humans have clay feet. People go onto r/Buddhism and ask who is enlightened right now? Who is the best teacher? What is the best sect? How do I get a valid teacher?

Those questions and those journeys are the spiritual life. They even split you at the point whether you go Mahayana or Theravadan. To recommend the Lotus Sutra over the Udana is a choice. To recommend Milarepa over Pali Canon is a choice. How do you make that choice? 

There was a person who was shot in the head, and it severed the part of his brain connected to his emotions. He seemed OK, and they sent him back to work. What do you want to have for lunch? He could not stop considering all the possibilities. You need your emotions to eliminate options. There are lots of options. Making a choice is maybe more complicated than it appears to be to those who have found a sangha. 

Connecting to a sangha can be hard. Some countries don't have a sangha. Some places don't have a sangha close by. Some cities are filled with ethnic sanghas that make people weird if they don't look like everyone else. It's a kind of turning of the tables, white people aren't too concerned when black people walk in, but there are cases where people who aren't white don't feel comfortable going to a Buddhist sangha in America. White fragility makes it hard to discuss that experience. Some people have psychological problems going to new places, risking new experiences. For me online experiences aren't very gratifying, but something is better than nothing. 

Reading books can make you develop the motivation to find a sangha, but it can also further reinforce the rugged individualism and irregular steps on the path. Take regular steps. Connect with a sangha. That is a choice that eliminates other options but not making a choice is a choice that eliminates other choices too.

For me, A Survey of Buddhism by Sangharakshita is the amazing classic from 1947 that nobody talks about enough. He has so many amazing books. That's coming from someone who was raised in the Triratna sangha. 

There are other Buddhists who don't consider Triratna a real sangha. We could talk about calling people in a sangha wrongheaded, but the fact is we do judge other people's sanghas, and do have ideas about which ones are good and bad. I think Shambala is irredeemable. R/Buddhism has a list teacher to avoid. Sex and the Spiritual Teacher by Scott Edelstein is an essential classic that teaches the spiritual seeker some important things. That might make someone think everyone is a sham when there are plenty of teachers out there who want to teach people. The model of friendship and taking responsibility for your spiritual life is the best. That developing spiritual friendships isn't easy in this day and age, doesn't take away the fact that friends can really help us. Authors and books can give some one way communication that is a kind of sharing of minds. Shoes Outside The Door is another book about scandal in the sangha. 

I've mentioned history of Buddhism. A Short History of Buddhism by Andrew Skilton is interesting, really specific about early schools. Mahayana Buddhism by Paul Williams. The Circle of the Way by Barbara O'Brien. Zen Baggage by Bill Porter is his pilgrimage to various Chinese Chan sites.

I really like memoirs and biographies of Buddhist lives. Nanamoli's The Life of the Buddha is a good start.

There's a really good blog about Buddhist fiction. Buddha Da by Anne Donovan was my favorite novel.

I really like reading. Reading is a spiritual practice. Soaking up the culture from around the world through words is in a way a miracle to me. 

I don't think you have to take an intellectual approach and many teachers would say being mindful and kind is more important that reading.

Links:

I tried to answer the question once before.

I've tried to express which books helped me how.

As usual Sam Littlefair has a good answer