I will be DMing a group of new players soon. For the first few sessions, I'll be doing one-shots to teach them the basics and to give myself experience DMing. After that, I've had my eyes on Dragon Heist for the first real campaign. I saw the levels 1-5 and assumed it was beginner friendly, but I want to make sure. Is this a good idea? Also, (Potential spoilers for Dragon Heist following, although I'm not sure you would consider it to be a spoiler) is there an ideal villain/season to run? Thanks in advance for anyone who replies to this.

I’m a very new DM, pretty inexperienced in running anything besides one-shots, and I did Dragon Heist as my first real campaign. 

I loved it. I can’t say much for comparing W:DH to other first-level official adventures, but you can’t go wrong with Dragon Heist. 

There’s a lot of preparation that goes into it, but I’m sure that fact comes with the DMing territory. I found that the book does really well with explaining what you need to know, even if you get off-track.

As for new players. Be sure to explain that there is very little combat in this campaign. My group loved that fact, but not everyone will.

i won’t say that there’s an ideal season to run. I did Winter and enjoyed it. I found a lot of people on here went with Summer and they enjoyed it. 

Currently, Dragon Heist and Waterdeep have influenced nearly all our adventures since then. Either we’re meeting old characters who are now influential, or we just use Waterdeep as our setting because we all know the ins-and-outs. Great fun, and I don’t think you can go wrong with it. 

Dragon Heist is a very... Customizable module. The adventure itself is very basic and short, which might be right up your alley, but the book provides a lot of source material to make your own story out of it. You can start by running it as it is, and then maybe build upon it if you and the players want to continue.

As for villain, they all have some unique flair that makes them fun. Keep in mind though that choice of villain does not impact the story that much, since the players are very unlikely to interact with them (with the exception of Jarlaxle and maybe the Cassalanters).

• Xanathar - This guy's a lot of fun. He's completely off the rails crazy, and probably the best villain to run as an actual boss, since he has all the fun of a beholder with a distinct personality. If you don't plan to run it beyond the adventure in the book, though, I wouldn't bother.
• Jarlaxle - Probably the best for roleplaying, he is very over the top and fun to role-play. I would reccomend watching a Sean Connery movie or two to gain inspiration. The villain the players are most likely to interact with in the basic adventure.
• The Cassalanters has by far the most interesting servants (devils), and provide a great moral conundrum. I would reccomend having them interract with the players in some way, maybe as potential sponsors for the Trollskull tavern? Also, if you run these two, have the players meet their children, maybe they get lost and ask the characters to help them get back home, since that will make the moral conundrum worse.
• Manshoon - He sucks, and I think he's boring.

I'm pretty new to DMing and havent run Dragon Heist personally but it seems like a solid module for both new DMs and players. From what I've seen skimming the module it looks very sandoxy/freeform so if you want to stretch your creative wings as a DM it sounds perfect. It does seem pretty beginner friendly from what I've seen but more work from the DM. As far as premade modules that are good for both new players and DMs I'd personally recommend Curse of Strahd (granted i may be biased because that's the first module I DM'd) because it has potential hooks for every available area and is very good at describing whatever area you end up in.

Dragon Heist provides some decent background material for Waterdeep adventures as well as establishing a party of adventurers with a headquarters in the city. WDH has 4 possible villains and enough information that any of the four can be used for the playthrough. It has some replayability with different groups by choosing different villains or you can expand on it with your own material using the sources in the back for guidance.

WDH can also link to Dungeon of the Mad Mage or alternatively to the dungeons included in the Tales from the Yawning Portal source book. The characters could basically either hear rumors or be hired in Waterdeep as a hook to become involved with whatever adventure you want them to take on next.

WDH probably has more social encounters and fewer combat encounters than a typical module so this could make it a bit more challenging to DM.

As an experienced DM, I hated it when I ran dragon heist. The adventure was sold as "... a mad romp through the wards of Waterdeep as you uncover a villainous plot involving some of the city’s most influential figures. A grand urban caper awaits you. Pit your skill and bravado against villains the likes of which you’ve never faced before, and let the dragon hunt begin!"

It is not. The only heist is the one that happens before the game even begins. It essentially boils down to

• Level 1: Basic Intro Stuff (probably the best written section outside the villain chapters)
• Level 2: Into to Faction Quests
• Level 3: McGuffin Hunt Begins (oh BTW, your party is supposed to go the the temple of gond, but it isn't introduced until they are supposed to go there, so the PCs don't even know its a thing that exists. I gave one of my PCs a tie to the temple and wrote a faction quest for them to do in Chapter 2 to handle it).
• Level 4: 10 encounter chase scene where you string the party along.
• Level 5: Vault, and so anti-climactic its sad.

The plot is linear with the exception of the faction missions, which boil down to simple combats or single skill checks. And in those faction combat encounters, do you think that Wizards thought to give you a map? For example, the Harper's 3rd Level, fight a gazer in a book shop? NO!

It was more work than I wanted to do for a decent adventure.

In my experience, the original Dragon Heist is an interesting idea with a flawed execution. As Houligan notes, what the adventure advertises and what it actually is are two very different things. Also, the central mystery driving the adventure is a bit shallow and has several clear plot holes.

If you're looking for a version of Dragon Heist that follows through on the promise of the adventure, try this remix by Justin Alexander. The rewrite is a long series of articles, but it's entirely free.

The beauty of the remix is that the party ends up interacting not just with one villainous faction, but with all of them. And better still, it involves not just one heist, but several! I haven't had the chance to run this remix myself yet, but I'm very impressed by the changes and by the way it's organized. Not only does it vastly improve on the original adventure, but it's also packed with additional content. All and all, it's a much more fully realized version of Waterdeep.

If you check out the rest of the site, there's also some cool supplemental content, like this article series on making better use of the tavern the PCs open at Trollskull Manor.

Another option to run is the adventures from Saltmarsh. Reading through the 1st level adventure, I like it a lot better than Dragon Heist.

Also, the guy jreggers linked to has a review of Dragon Heist that fits what I think of it.

So here’s the big question: Do I recommend Dragon Heist?

…

… how much work are you willing to put into fixing it?

I came to Dragon Heist because I wanted something that I could basically run out of the box. That’s not really what I found: I could probably technically run it as written, but I wouldn’t feel good about myself as a DM. So, for me, Dragon Heist is a failure.

I think it's more of a "Your Mileage May Vary" situation. As a counterpoint to the thread's current sentiment, I had a wonderful time DMing Dragon Heist with Jarlaxle as the villain and now I'm running it again for a less experienced group using Xanathar as the "Big Bad." So far my players are really enjoying themselves.

How much customization did you have to put into it though? My players also liked Dragon Heist after I ran it, and when some of them looked through it after we finished, they also immediately noticed some of the stuff that I had to fix.

As a "my first adventure to DM" I think it misses the mark. With more work than I expected, you can get a good story from it though.

Not as much as you all seem to intimate here, though I will admit that, as an experienced DM, there may have been some changes that I just subconsciously made along the way that doesn't register for me. I had plenty for my first party to do since they were intertwined with about four or five factions, plus I gave them a little room to breathe and explore the city and learn about places before the fireball chapter kicked off. 

For me, the biggest issue was a lack of basic stuff, the two biggest being no maps for faction events and no magic items to be found anywhere. The latter one makes me think that this was written with AL as its target audience. Magic items don't matter because your players earn treasure points and couldn't keep the items anyway.

In all those factions quests that your party would have done, what did you use for battle maps? Having to come up with something for each of those encounters is why I wouldn't necessarily recommend for new DMs.

A specific example, the Emerald Enclave Level 2 faction quest, as written, and how I had to fix it:

Hook

“Outlying farms are being terrorized by a scarecrow come to life. It has slaughtered livestock, chased horses, and spooked farmers. No people have been killed as yet, so the City Guard is dragging its heels. Something must be done!”

Encounter As Written

Not one but three scarecrow are terrorizing Undercliff. One wears a sackcloth hood, another has a rotting pumpkin head, and the third is covered with a threadbare blanket. Characters who camp in a field for the better part of a day or night have a 10 percent chance of encountering one of the scarecrows. The attacks continue until all three scarecrows are destroyed. Reward: Each Emerald Enclave character gains 1 renown for ending the threat.

My Thoughts About It

First, why do the city watch not care about a threat to the cities food supply? Next, I had a party of six, which makes a single CR 1 monster trivially easy. There is no guideline in the book for how to scale this up or down (yes, there are in the DMG). It could have at least said "if your party is very capable, consider having them encounter more than one of the scarecrow at a time". There is no battle map or description of where you would encounter the scarecrows, just what they look like.

There is also a lot of wasted time of "We go to the fields, nothing happens, repeat"

How I Fixed It

Additional Scene Description to read when the players first go to the fields: Wheat grows tall in the farmers fields, hindering your progress. Part of one field has been cleared, with a single 5 foot hay bale surrounded by 15 feet of cut stalks gathered before farmers abandoned the task for fear of attacks. A road runs by the south edge of the field and some ravens are perched on top of the bale.

Things that can happen as the PCs investigate:

• A DC 11 Persuasion or Intimidation check when interviewing the farmers reveals that a Swarm of Ravens is spotted before each scarecrow attack
• A DC 15 Perception or Arcana check reveals that the ravens are supernatural in nature.
• If the swarm is killed before flying away (2 turns) all the the scarecrows are regular scarecrow.
• The players can help harvest the fields to remove the cover

The fight happens on whatever night the PCs first investigate. Some box text to read when it does: You see three slender figures to the north-east start to push through the fields towards you. As they get closer, you see they are scarecrows. One with a sackcloth hood, one with a rotting pumpkin head with a blue gleam in its eye, and the third covered in a threadbare blanket.

Toughen the encounter: the scarecrows are encountered all at once, and the pumpkin head one is replaced with improved scarecrow

Add some mechanics

• The crops in the fields provide 1/2 cover to creatures in them (+2 AC and Dex Saves)
• A critical miss with a fire based attack will set the fields on fire
• The hay bale in the field provides 3/4 cover (+5 AC, Dex Saves)

After the fight: If/When the PCs investigate the scarecrow remains, they discover that the blue gleam in the pumpkin headed scarecrow is a Spell Gem (Lapis Lazuli) with Ray of Sickness in it.

Well, since 5e is built more for a "theater of the mind" experience, a lot of those faction missions were just described as needed and the combats were run without maps. Many of those fights wouldn't be grand enough for me to even bother drawing out a map or replicating one that was provided in the book.

As for the Emerald Enclave scarecrow mission, I just had the party stumble upon more than one of the scarecrows since the party was large enough to make a single scarecrow an easy encounter.