The quickie teach-newbies-D&D game I was planning to start this weekend got bumped to next weekend, which actually helps because there’s a bit more work in converting The Keep on the Borderlands to (what I consider) a playable 5E adventure than you might think. Just going through and giving the NPCs names rather than THE CASTELLAN and THE CURATE is a fair amount of work. On the other hand, last night I had a sudden inspiration as to what the “Caves of Chaos” were actually all about (and why there is effectively an apartment complex with six different types of humanoids all living together), and suddenly the adventure goes from THE MOST GENERIC D&D CRAWL EVER to actually having a theme and potential for cool stories.
Milk Run Or Meat Grinder?
I’m a little concerned about the difficulty scale. KotB was designed to take characters from roughly 1-3 in the original “basic” D&D, in which thieves levelled up fairly fast and wizards levelled up glacially slow etc. You could expect the overall level of the party to remain stable at a given level through several sessions. Modern games pretty much have everyone progress at the same pace, and that pace is mighty fast at low level. If I put in encounters that are balanced for 1st level characters, they’ll be like tissue paper just a few sessions in when the characters have all jumped to 3rd.
That’s not a problem per se– with a good mix of encounters it’s not a problem if the party blows through some of them– but it is something I have to be aware of. In a sandbox environment (which KotB mostly is, albeit a small one), there’s a real danger of the players getting in way over their heads. Play reports from KotB across all editions are rife with stories of TPKs or near-TPKs, because the party killed a couple of goblins, got cocky, and suddenly found themselves facing 20 more when the alarm went up.
(Yeah, pretty sure everyone in the party was at least 3rd level by that point.)
I recently read a blog post in which the author opined that D&D can basically be played two ways: first is a group of stalwart adventurers slaughtering monsters and reaping great rewards, while the second is a black comedy in which a bunch of ne’er do wells throw themselves into deathtraps, get slaughtered in horrifying ways, and occasionally escape with a few bits of gold to show for it. Modern D&D, the theory goes, aims more for the former, while old-school D&D was more of the latter.
I don’t entirely buy this– I played old-school D&D when it was still pretty young school and while we did have some entertainingly horrific character deaths (“eaten alive by mutant cannibal smurfs” is one that made a lasting impression), it wasn’t quite the meat grinder it’s sometimes made out to be. Maybe it was just our group, but I remember the general consensus was that if you were in a game where the DM was eager to kill the characters, it meant the DM was an ass and you just didn’t play in that game again. 
Finding Traps: Pick a Skill Already! And Other Concerns
I love 5E. Like, really love it. It plays fast, furious, and fun in a way I haven’t really seen since Tunnels and Trolls, but is rigorous enough that it has meat to latch onto for building unique and interesting characters, scenarios, and challenges.
However, as with all new editions, it has its rough spots. It still doesn’t quite know what to do with rogues, for instance. I’ve talked before about the rogue problem, and while 5E does bring back Thieves’ Cant, it has decoupled burglary from the rogue class entirely, putting that stuff mostly in the realm of “thieves’ tools proficiency,” and keeping the rogue class as a situational damage dealer. (What that means is that anyone who wants to learn the tool proficiency can be the party trap-disarmer and chest-unlocker, which is part of 5E’s “party role not required class” philosophy, and that part is actually fine, thumbs up!)
In their apparent rush to put something in for thieves to do, without really having much in the way of a solution to the rogue problem, they have left a lot of the whole traps and locked doors bit with very sketchy implementation at best. Random dungeon hazards have a Perception DC that compares not to the characters’ check, but to their passive Perception check. So… the characters either always pass or always fail? What’s the point of that? As a DM, creating adventures for your own party, you know what the characters’ passive Perception is. If you assign a DC, you already know if the characters will pass or fail. It’s silly.
Then there’s the Perception vs. Investigation thing. On p. 178 of the Players Handbook, under Investigation, it says “When you look around for clues and make deductions based on those clues, you make an Intelligence (Investigation) check. You might deduce the location of a hidden object, discern from the appearance of a wound what kind of weapon dealt it, or determine the weakest point in a tunnel that could cause it to collapse.” That, combined with the fact that the Starter Set pregen rogue had proficiency with Investigation and not Perception, suggests that Investigation is the intended skill for searching for traps, right?
Except right next to that is a sidebar called “Finding a Hidden Object,” in which it clearly says, “When your character searches for a hidden object such as a secret door or a trap, the DM typically asks you to make a Wisdom (Perception) check. Such a check can be used to find hidden details or other information and clues that you might otherwise overlook.”
So… you make a Perception check to spot details, and then an Investigation check to interpret them? I can see that being worth the effort for some “the entire room is a giant deathtrap” puzzle, but for every locked door and chest?
In my games I tend to split the difference– if there is a spottable trap (e.g., a trapdoor or a pressure plate), I set the DC and tell the players “You’ve walked into a trap. Make a Perception check to see if you spotted it in time!” If the trap is hidden in a mechanism (such as a locked chest) or if the characters are actively on the lookout for it rather than “passively perceiving,” so to speak, I call for an Investigation check. It annoys me that a system that was famously publicly playtested for two years still requires house-ruling like that, but nothing’s perfect.
Magic Item Construction Rules– As In, There Aren’t Any
This is an interesting divide. One of my players has been very disappointed in the way 5E not only “doesn’t really have” magic item construction guidelines, but at how it was deliberately removed from the game as a going concern.
What interests me most about this is that when 5E came out, this was something that a lot of people in the discussions I followed stood up and cheered about. “Goodbye to the Magic Shop Economy, and good riddance!” about summed it up. Reasons for this varied from “It sucks all the mystery out of magic items!” to “Conan never went to a magic shop!” to “Hooray, I don’t have to math-check another twinked out game-breaking magic item again!”
For myself, I didn’t have such strong feelings on the matter. I did think the whole magic item economy contributed to the ever-increasing rules overhead of the 3.x/PF era, but I also understood the reasoning that went into it. If your campaign didn’t assume “build a keep and retire” as the characters’ endgame, and didn’t have built-in money sinks like paying for training to raise levels (both of which were pretty much gone by the end of 2E), well you had to have something to spend all that gold on, and effectively having magic items as their own progression/character customization track would seem to kill two birds with one stone.
On the other hand, once upon a time DMs stocked dungeons with magic fountains that made weapons do double damage, or randomly turned characters into bugbears, and “game balance” wasn’t even an issue. When did we all get so obsessed with finely-tuned math within a game that’s theoretically all about letting your imagination run wild?
In any case, Josh (the player in question) not only did not stand up and cheer, he considers the lack of a robust magic item creation system to be a major failing on the part of 5E, and his reasoning is sound. Having a system spelled out in black-and-white removes a lot of the vagaries of system mastery. “Is ‘vorpal’ a game-breaking property at 3rd level? Well it adds +10,000 gp to the price, and that’s more money than the entire party has put together at the moment, so yeah, it must be. On the other hand, ‘shock’ only adds +3,000, so it must be legit.”
It also means the player has more control over how their character develops. If your whole character concept is based around having a Captain America-style shield that you can throw around and bang off mooks’ heads, you don’t have to hope you get lucky and the DM stocks one in the dungeon somewhere, you just save up your gold until you can afford to buy the thing.
And finally, as already alluded to, it gives the characters something to do with all that treasure they cart home from the dungeon! Josh particularly spoke in glowing terms of that moment of striding into town with bags full of gold itching to be spent and seeing what could be done with it, something I refer to as the Candy Store moment. And honestly, I can totally see that, although it also has the darker side of the “high level item tease,” where vorpal swords are there on the theoretical shelf, but you’ll never be able to afford one.
I don’t think this is an issue with a “right” or “wrong” answer, just preferences. MMOs and similar games particularly have made the gear-as-progression model a style that people are used to and expect, whereas someone coming from an era in which finding a +1 sword was notable, but you could also randomly become immune to all poisons because you kissed the statue of a goddess, is going to be a lot more comfortable with (or at least resigned to) DM fiat.
I’m working on ways to split the difference– I want to give Josh his Candy Store moments, but I also don’t want to have to retro-fit the magic item economy back into the game. I’ve set up a potential “magic shop” situation in my Keep On the Borderlands adaptation, but it’s hidden and will take some digging to find it, even assuming the characters manage to amass enough loot to make buying magic items a feasible concern.
In any case, hoping for some fun. If the game takes off, maybe I’ll pull out The Lost Caverns of Tsojcanth and let the players argue over how that’s supposed to be pronounced. 😉
 This is not a criticism, it was written in 1978? 79? to be an introductory module teaching would-be DMs the basics of adventure structure, and giving would-be players a taste of how the game was supposed to go. Its very existence pushed the envelope of D&D, the design within didn’t have to. Today’s equivalent is the Lost Mine of Phandelver, from the 5E Starter Set. But half the group just went through that in my game, I can’t just run that one again!
 Unless the adventure in question was The Tomb of Horrors, but even back in the day that was pretty clearly its own distinct experience compared to regular campaign gaming. I met a few DMs who seemed to think ToH was what every adventure should be all the time. I didn’t stay in their games.