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Where's a good place to start?

I recommend EX MACHINA by @Christopher as a really good "beginner's novel" for a lot of Star Trek fans too because it's a direct sequel to ST: TMP. You may miss some of the jokes if you don't know the production notes or their weird new races but it actually does give a showing of just what the novels are capable of, which is expanding on the themes and ideas of the show as well as stories in way you wouldn't normally think about.

In this case, Kirk reflecting on his failures in the movie as well as history of dealing with Rogue AI.
 
I am a big fan of DEBTOR'S PLANET by W.R. Thompson. It's a TNG novel set during the middle of the show's run that deals with Ralph Offenhouse (that hedge fun jerk who was cryogenic-ally frozen and found by the Enterprise in TNG season 1) as a Federation ambassador to the Ferengi as well as some political machinations between The Federation, the Ferengi, and the Cardassians. It also has a scene with Riker, Worf, and Data watching awful direct-to-video action movies from the 80s, which is hilarious.
 
Oh, and Articles of the Federation by KRAD. Probably non canon now, sadly, but...read it !

Actually, having recently re-read Articles, it seems that virtually the entire novel still works quite well with the new canon Picard-verse continuity in the broad strokes -- there's one section in particular (the chapter where B-4 is declared a sentient being) that might superficially seem to conflict with PIC, but given that this sequence takes place some years prior to the Mars synth-attacks, is pretty easily handwaved away (like perhaps the Federation rules in his favor, but then he ends up getting dismantled and stored in Dr. Jurati's laboratory regardless).
 
Marco is working as a senior content producer at Realm Media, which creates audio dramas in various genres. I met with Marco back in January; we grabbed a quick lunch and talked about the possibility of me pitching a project to Realm, which I did. We were almost good to go, but the deal fell apart at the last minute, so I'm back out in the spec-submission wasteland.
I recently started a couple of Realm series, The Bullet Catcher, and Born to The Blade. Do you have any idea if Marco was involved with them?
 
If you are a Next Gen fan then I would check out anything Peter David did, but Imazdi and it’s sequel are two classics to get your feet wet.

For Picard, I would check The Dark Veil as previously suggested as it is a Riker and Troi backstory adventure, while the first Picard novel is very well written but very grim to start reading Trek books as it has to sell where the characters and Federation are at the start of the show.
 
If you are a Next Gen fan then I would check out anything Peter David did, but Imazdi and it’s sequel are two classics to get your feet wet.

For Picard, I would check The Dark Veil as previously suggested as it is a Riker and Troi backstory adventure, while the first Picard novel is very well written but very grim to start reading Trek books as it has to sell where the characters and Federation are at the start of the show.

I found the Peter David Q novels very entertaining when I read them back in the 90s.

I guess to your point about that novel being grim has anyone classified the novels in terms of tone. For example, what novels are comedy versus ones that are more serious? Sometimes I'll be in a mood for fun Star Trek adventure. Other times I'll want something more serious.
 
True. I have no problem with stakes but I think the first Picard novel is so grim by necessity of the premise that it is hard to recommend as a jumping on point.
 
I recently started a couple of Realm series, The Bullet Catcher, and Born to The Blade. Do you have any idea if Marco was involved with them?
According to facebook, Marco produced The Bullet Catcher. He's never mentioned Born to the Blade.
 
I’m just getting back into reading the Trek novels after around twenty years of basically “collecting” them (buying all of them with the intention of reading them eventually but “eventually” didn’t come until twenty years later) from around the start of TNG (going back and also buying all of the Bantam and Pocket TOS books that were out at that time, too) through the DS9, VOY, and ENT on TV years, to around 2011 when I stopped buying comic books and novels on a regular basis.

Flash forward to two or three years ago and I started using my local public library regularly for checking out books to read (both print and eBook), including the newer Discovery and Picard novels. At this point I’ve read the first three of both of those series.

I knew I wanted to get back into the older Star Trek novels, but, as you said, it can be a bit overwhelming deciding where to start? TOS? (If so, how far back, and in what order?) TNG? Enterprise? (The last time I’d started doing a reading of Star Trek novels it was beginning with the Enterprise novels, but then I got only half a dozen or so books in before putting that one on indefinite hold.) And do you start at the beginning with those TNG era novels or at some point later on. (The problem with starting any of them at the beginning is realizing it it will take a very long time to get to the more current releases.)

I’ve decided to start upon several different “paths” at the same time. I’d already started on one path, the Discovery and Picard novels. I’ll continue along that path, reading those books from time to time.

My second path I’ve decided upon (since I’ve been in a TNG mood) has been to start reading (in some cases rereading) the TNG novels, starting just after Star Trek Generations, as I see the loss of the Enterprise-D as a clear separating point between TNG “the TV series era” and TNG “the movies and beyond era”. I’ve looked at various timelines posted online and come up with a rough reading order. I started with Ship of the Line first, and am currently reading the William Shatner “Shatnerverse” novels starting with The Return. I also have asked my public library to get the six part “Slings and Arrows” ebook series so I can read those, too.

Eventually, I’ll add in the various other series into this reading “path” (DS9 starting with A Stitch in Time and Avatar, VOY with Homecoming, and New Frontier, SCE, Titan, etc.), eventually getting me into the “litverse” proper (which I’ve never read).

I’m thinking my third “path” with be the movie era TOS books starting with TMP, as my own personal “golden age” of Star Trek was the 1980s and early 1990s, when what was new was the TOS movies and TNG.

A fourth path would be picking up where I left off in the Enterprise novels, or starting TOS at the beginning with the James Blish episode adaptations and the Bantam novels, or the TNG, DS9, and VOY novels overlapping with their TV series, time frame wise.

There are so many choices. It really depends on what part of Star Trek appeals most to you. Figure that out first and then just dive in. You may want to start with a shorter series, like the much recommended Vanguard or Titan series. Or start something a bit more ambitious like the Litverse from the very beginning. Or, you might just want to jump around the many done-in-one TOS novels. Whatever hovers your Runabout, as they say!

—David Young
 
And if you want to be able to find most of the Star Trek books you want to read, you'll need to read eBooks.
 
I’m just getting back into reading the Trek novels after around twenty years of basically “collecting” them (buying all of them with the intention of reading them eventually but “eventually” didn’t come until twenty years later) from around the start of TNG (going back and also buying all of the Bantam and Pocket TOS books that were out at that time, too) through the DS9, VOY, and ENT on TV years, to around 2011 when I stopped buying comic books and novels on a regular basis.

Flash forward to two or three years ago and I started using my local public library regularly for checking out books to read (both print and eBook), including the newer Discovery and Picard novels. At this point I’ve read the first three of both of those series.

I knew I wanted to get back into the older Star Trek novels, but, as you said, it can be a bit overwhelming deciding where to start? TOS? (If so, how far back, and in what order?) TNG? Enterprise? (The last time I’d started doing a reading of Star Trek novels it was beginning with the Enterprise novels, but then I got only half a dozen or so books in before putting that one on indefinite hold.) And do you start at the beginning with those TNG era novels or at some point later on. (The problem with starting any of them at the beginning is realizing it it will take a very long time to get to the more current releases.)

I’ve decided to start upon several different “paths” at the same time. I’d already started on one path, the Discovery and Picard novels. I’ll continue along that path, reading those books from time to time.

My second path I’ve decided upon (since I’ve been in a TNG mood) has been to start reading (in some cases rereading) the TNG novels, starting just after Star Trek Generations, as I see the loss of the Enterprise-D as a clear separating point between TNG “the TV series era” and TNG “the movies and beyond era”. I’ve looked at various timelines posted online and come up with a rough reading order. I started with Ship of the Line first, and am currently reading the William Shatner “Shatnerverse” novels starting with The Return. I also have asked my public library to get the six part “Slings and Arrows” ebook series so I can read those, too.

Eventually, I’ll add in the various other series into this reading “path” (DS9 starting with A Stitch in Time and Avatar, VOY with Homecoming, and New Frontier, SCE, Titan, etc.), eventually getting me into the “litverse” proper (which I’ve never read).

I’m thinking my third “path” with be the movie era TOS books starting with TMP, as my own personal “golden age” of Star Trek was the 1980s and early 1990s, when what was new was the TOS movies and TNG.

A fourth path would be picking up where I left off in the Enterprise novels, or starting TOS at the beginning with the James Blish episode adaptations and the Bantam novels, or the TNG, DS9, and VOY novels overlapping with their TV series, time frame wise.

There are so many choices. It really depends on what part of Star Trek appeals most to you. Figure that out first and then just dive in. You may want to start with a shorter series, like the much recommended Vanguard or Titan series. Or start something a bit more ambitious like the Litverse from the very beginning. Or, you might just want to jump around the many done-in-one TOS novels. Whatever hovers your Runabout, as they say!

—David Young
I really like the different paths approach too. I have one for the Gold Key and Bantam comics and books, one for basically everything from when Simon and Schuster took over the license plus all the comics from the same era, one for Kelvin, one for IDW and one for the post-Discovery books.
 
I'm also in favor of "different paths" or, as I call it, "bouncing around". I used to try to just read everything in a series in order, or go through the LitVerse in order, and I'd burn out or bounce off a book or whatever. Much more manageable to give yourself the freedom to bop between series and authors and time periods without getting too stuck on a particular list.
 
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