What books should I buy?

We've probably now seen the last V5 book published (Courts of the Damned). I have all of them (mostly on PDF, but quite a few in hardback too). Which books you need depends on the game you want to play and your own experience with the game. Here's my opinions to try to help you decide where to invest. This list is from https://vtm.paradoxwikis.com/Official_TTRPG_sources - I'm not including most of the smaller PDFs or Stories (like the Monsters, or New Blood, etc) - I'm concentrating on the core source material, the larger traditional hardbound books, with a few exceptions where they are tightly tied to a larger book.

If you can, I find all of these books more readable in hardcover, but I picked up almost all of these in a Humble Bundle pdf sale at a fraction of the retail price. If you see that, I recommend that option.

The Books

Vampire: The Masquerade Corebook

This is an obvious must have. It has the core rules in it. It is a bit of layout disaster, but if you buy one book, it probably should be this one. 

Vampire: The Masquerade Players Guide

If you are buying two books, this should be the second. It expands out all the clans to cover the full 14. It has additional Merits, Flaws, Backgrounds, Disciplines, etc, expanding out the game. It has some clarified and simplified systems (like Projects) as well. A little better laid out than the core book to boot.

Vampire: The Masquerade Camarilla / Vampire: The Masquerade Anarch

Discussing these two together - I don't think either of these books are particularly strong. They do have good information about telling Camarilla vs telling Anarch stories, but if you already know the general lore and setup around Camarilla and Anarch, I'd not bother with them. If you don't know that lore and context, then consider picking up the one that most closely matches your Chronicle, but frankly, I think you should pick up Courts of the Damned over either of these to get information about how both Camarilla and Anarch domains work.

Vampire: The Masquerade Sabbat The Black Hand

This is all about the Sabbat as antagonists. If you're interested in bringing in that or want more Lore information about the Sabbat, this is a good book, but I haven't pulled a lot of value out of it in my own game.

Vampire: The Masquerade Second Inquisition

I look on this similar to the Sabbat book - there's lots of good information here for those that want the Second Inquisition to have a large role in their Chronicle. There are lots of weapons, lots of antagonists, and a good amount of lore in here. I personally don't find the Second Inquisition that interesting to have front and centre, but a well put together book if you are interested in the SI.

Vampire: The Masquerade Chicago by Night /  Vampire: The Masquerade Chicago Folios / Vampire: The Masquerade Let the Streets Run Red

Chicago by Night is the city sourcebook for Chicago, with the Folios and Let the Streets Run Red adding Chronicles and Stories and hooks in for the area. Full of SPCs and story points. I think Let the Streets Run Red is potentially a great first Chronicle for new STs. I steal stat blocks and reference SPCs from these often. I really like having these on my bookshelf, despite never intending to play a Chicago based game.

Vampire: The Masquerade Cults of the Blood Gods / Vampire: The Masquerade Forbidden Religions, Vampire: The Masquerade Children of the Blood / Vampire: The Masquerade Trails of Ash and Bone

Cult of the Blood Gods and its follow-ons (Forbidden Religions, Children of the Blood, Trails of Ash and Bone) concentrate on the Hecata and then on various vampire Religions and Cults and beliefs. I pull a ton of things from Cult of the Blood Gods and Forbidden Religions - little references to things, weird SPCs - there's a lot of great stuff here to fill gaps in your own stories. If you are doing a Chronicle with the Hecata, Cult of the Blood Gods is a must have, but I think almost any Storyteller will get good stuff out of Cult of the Blood Gods and Forbidden Religions. Children of the Blood and Trails of Ash and Bone are smaller pdf add-ons, but can be somewhat useful.

Vampire: The Masquerade Book of Nod / Vampire: The Masquerade Book of Nod Apocrypha / Vampire: The Masquerade Revelations of the Dark Mother

If you have any players interested in ancient religions or where Vampires came from, the Book of Nod is a fantastic thing to sprinkle in and reference. It is basically the in-world Vampire bible. The Revelations are similar, though from a different perspective. The Apocrypha have some actual V5 disciplines added to it.

Vampire: The Masquerade Fall of London

Fall of London is a major Chronicle setting for Vampire the Masquerade V5. It advances the Metaplot (ie, the lore) quite a bit, introduces a number of significant SPCs and covers a wide range of information around London, the UK, and the happenings in the World of Darkness. It has a reputation of being a difficult Chronicle to run. I've made some scant references to the events of the Fall of London Chronicle in my games, but I don't consider this a must-have book.

Vampire: The Masquerade Blood Sigils

Lots of additional information around Blood Sorcery and Thin Blood Alchemy, magic and relics. This is well worth grabbing. I'm not sold on the black market described in this book, but there's a lot of good stuff here beyond that, including the ability for players to create rituals for Blood Sorcery. Worthwhile picking up if there's any sort of interest in magic in your Chronicle.

Vampire: The Masquerade Blood Stained Love

This book covers romance and power dynamics in Vampire. It has a lot of information about the in-character and out-of-character concerns with this style of role-playing. I really like this book, but not everyone does - some people are concerned about these topics in games, some people just don't like its content. I do recommend it if you have any intention to cover romantic tropes in your Chronicle.

Gehenna War / In Memoriam

Putting these two together. They are both books that include information about including and playing older vampires, elders and methuselahs, adding quite a bit of lore. New rules and systems, more stats and abilities. I like In Memoriam more, mostly because I have no interest right now in telling a Gehenna War story - if you do or want more information about the Gehenna Wars and the Beckoning, pick that one up. Gehenna Wars also includes a lot of combat focussed systems intended for Chronicles with a high amount of combat.

Vampire: The Masquerade Crimson Gutter

This is a Chronicle book that can be set in any city. I do recommend it if you are looking for Stories or short Chronicles, especially for a beginning Storyteller. It is a great guide for constructing or running a Chronicle, too.

Vampire: The Masquerade Tattered Façade

This is my favourite V5 book of them all. It is intended to give you more options for Horror in your Chronicle. There's coverage of different ways to tell horror stories and ways to add complexity or darkness to your game. New variants and rules around Disciplines and Powers. Different types of horror genres and interesting twists. Awesome book.

Vampire: The Masquerade Live from the Succubus Club

This is a very useful book for Storytellers considering telling stories around the music or entertainment industries, or stories about a nomadic Coterie, or both. Some smattering of lore and characters around Los Angeles, Chicago, and Western Europe. A discussion of mortal focussed Chronicles. A full sample touring band Chronicle is included. If your Chronicle focusses on any of these things, this is a really good book.

Vampire: The Masquerade Courts of the Damned

This book should be required reading for every storyteller of Vampire - and every player too. We've been missing this book for years. This book lays out how Vampire politics work - for the Camarilla, the Anarchs, the Independents. Lore, SPCs, helpful tips, structures and systems. Really usable for any edition of Vampire, this book is fantastic for laying out how to make a political game work. And every game has some element of politics, even if it is trying to stay out of the way of the powerful.

My Overall Recommendation

Here's my recommendation of what to buy in what order, for a new Storyteller. For a player, 1 and 2 are probably sufficient :

1. The Core Book - must have for everyone
2. The Players Guide - must have for everyone
3. The Courts of the Damned - this will make you better at running Vampire society
4. Tattered Facade - this will make you better at running horror

Everything else is situational - pick an enemies book, if you like (Second Inquisition, Sabbat). Pick up the religions and cults set (Cults of the Blood Gods, Forbidden Religions) if that's relevant, though I find both very useful. Pick up Live at the Succubus Club if entertainment, or mortals, or nomadic life are central. Pick up Blood Stained Love if you want romance to have a place; Gehenna Wars if you want something combat focussed or are really interested in the Beckoning. In Memorium if you want more information on older Kindred. Blood Sigils for Blood Sorcery and Alchemy. One of the Chronicles or Settings books (Chicago by Night, Crimson Gutter, Chicago Folios, Let the Streets Run Red, Fall of London) if that's relevant to you or you want a pre-written Chronicle to run. The Camarilla and Anarch books are much less relevant now that we have Courts of the Damned - pick them up for completion only.

I hope this was helpful to you in your V5 journey!