What struck me is that the mechanic was entirely random, other than being modified by a particular ability bonus. That is, the mechanic does not contemplate being influenced by the decisions of the players. How do you search? What are you looking out for? Are you asking for directions? Who do you ask? You can, of course make up modifiers on the spot. But the mechanic does not appear to contemplate that, and gives no guidance as to how modifiers should be assigned, or what would constitute a typical, unmodified search.
The second thing that struck me is that the majority of the possible results just related to how long the search takes, not to actual success or failure. And it is expressly called out that encounter checks should be made at regular intervals during the search. So effectively what players are doing is rolling for the number of encounter checks the DM is going to make.
This is true, but the mechanic should at least set a baseline, so you know which approaches should have a bonus, and which should have a penalty.In terms of what you reference above, I obviously don't know the supplement you are referring to, but I think the expectation about modifiers and how to perform searches is one of those assumed DM competencies (i.e. "a DM should already know how to do this").
I have a couple of relevant design rules I follow:I personally use a semi-random mechanic for city navigation (that is to say cities which need to be navigated anew - I don't apply it to well-known cities or small settlements) based on a Survival or Investigation check. Not entirely random, mind you, since different characters have better or worse check bonuses, but still determined by a die roll. Modifiers do come into play depending on specific circumstance, but being 5e, they are more in the "Advantage/Disadvantage" realm rather than "+X/-X" bonuses.
My players state their objective ("I'm looking for a place that sells _____"; "I'm trying to find a man who knows about ________"; etc.), and I set the DC based on difficulty. If it's a simple or unimportant request, it gets a low DC, or I just may just handwave it and say "You just want to find an inn? Yeah, there's one right on the corner". If it's a big request that requires wandering and asking around a lot, then the DC is tougher, and there is usually a penalty involved for bad failures (wasted time, picked pockets, corrupt city guards, walking down the wrong alley into a mugger's nest, etc.).
Unlike squeen's position, I believe that playing it out is the whole point. That's the game; you want situations to unfold, not to be dropped into laps like neat little packages. Wandering a strange city should feel like that - wandering. That's how you explore, those are your opportunities to showcase what the city is all about. The random things they encounter and the consequences for that wandering are exactly what breathe life into a city, otherwise your city is just "a place where stuff is". The trick is using a deft hand (see below).
This part I think is just vestigial rules from old-style dungeon crawling, and shouldn't be done. Time is generally not a valuable commodity when the party is outside in civilization; doubly-so if they are taking some downtime and are already killing time anyways. Routine random encounter checks in a settlement are more detrimental than beneficial, because:
1) players tend to split up in cities, so you get long sessions of each player doing like two (usually mundane) things while you (the DM) has to juggle ten different scenarios at once;
2) there is generally no time pressure hanging over their heads, and so no real punishment or stress is felt for delays (as you've stated);
3) it actively punishes the players for getting to know your city, who are just going to rent a room and hole-up for a week to avoid trouble;
4) if the party is split up, you get a lot of combat scenarios playing out between you and one or two party members, which bores everyone else at the table; and
5) it steers the party way off course, into a million little side-quests (which can be fine if they need to be moved, but not when it's mandatory).

With regards to No. 3, I'm not sure where you got the idea that I believe tedious /routine things should be played out all the time, because I don't. I suspect you think I meant that in regards to my response to squeen's (limited) contribution, but my intent of that retort was to point out that "playing it out" means going through the motions of city travel via an element of randomness (which I believe squeen was arguing against, albeit with almost no words or context to go off), because I do believe that city travel with a randomized element is valuable. However, as I state with my "you want an inn? There's one on the corner" example, I too agree that trivial tasks should not be drawn out. If players just want to buy some rope, it's almost always "ok, you go to the general store, they charge PHB prices for everything".3. Things that are routine or tedious should not be played out, I have to disagree with you on this one. Failing to find a nearby grocery store with decent fruit at the end of the growing season might be a genuine challenge for me personally IRL, but I am not diverting resources from the actual adventure stuff I have going on to play a "finding fruit" minigame. If the players want to do that, they can play My Sims. Ditto for haggling. I have one player who wants to haggle everything - not because he enjoys it, but because he's cheap. I refuse to waste precious playing time in haggling over the price of a new bow.
5. Mechanics should be somewhat transparent, so that the players can make informed decisions. Depending on how you implement it, I may have an issue with your setting a DC based on your assessment of the challenge of the task. Making it an ad hoc decision makes it difficult for the players to predict the risks and make intelligent choices. Player and DM can have very different ideas about how hard a task is, so at the very least, the DM and the player need to be in agreement as to what the character would know about the situation.
My personal play style tends to use randomness to determine not just success or failure, but also the degree of success or failure. If you roll up a 15 on a DC 10 check, you get a successful outcome, but rolling a 23 is a super-favorable outcome - for example, the difference between finding a shop that sells wands versus finding a shop that sells wands and is also having a sweet sale; likewise, rolling an 8 on a DC 10 means some kind of failure, but not as troublesome as rolling a 3 - the difference between not finding a contact who can smuggle you into the castle versus being ratted out to the town guard for even daring to ask around. As my prerogative, the degrees and consequences of the rolls are always adjusted on the fly, as befitting a DM running a dynamic world.I think true randomness should be reserved for content creation or resolution of trivial matters. For anything that is non-trivial and has a direct impact on the characters, I think there needs to be an opportunity for the players to make decisions that can affect the outcome, even if they choose not to take advantage of that opportunity.
Hoes, thots, thirst-traps... you get the idea. Lots of Brazilian butt-lifts on Instagram. It's a hive of the self-absorbed; Narcissus would weep.Skanks?
The very first thing my (second) wife said to me was "You play D&D? That's so cool! What class do you play?"Did you guys see that new psych poll about things women find attractive? I was born about 40 years too early. Now - they claim - the most attractive hobby a man can have is reading. Playing D&D only came in at 53% unattractive! When I was 13 I think it was 153%.
I mean, back in the day the English majors I knew always used to get laid more than the engineers and athletic majors.Did you guys see that new psych poll about things women find attractive? I was born about 40 years too early. Now - they claim - the most attractive hobby a man can have is reading. Playing D&D only came in at 53% unattractive! When I was 13 I think it was 153%.