Permanent Progress

There is a certain mindset which I believe I have noticed in a few old-school DMs.  An idea is present within their minds that anything the player characters obtain is just another means to attack the characters.

Did you hire a henchman? Well, now he may or may not betray you.

Did you build a stronghold? Well, now it might just get attacked.

Did you get treasure from the dungeon?  Well, now it might be stolen in the night, or while you're away from your stronghold.

Is this a problem? No.

But, if you choose to run the game like this, your players will stop going to get treasure, stop hiring henchmen and stop building strongholds.

How can you be so sure?  Because that is exactly what happened.  Here is how I think things went:

The old-school DMs ran their games, and then in the 90s the players coming into the hobby, with the majority being power-gamers, saw the weaknesses of treasure, strongholds and henchmen for what they were, and simply stopped using them.  Consequently, the third edition of the game, and 3.5e, did not include rules for dungeon delving, henchmen, or strongholds, because the players, at least the new majority, had stopped using them.

 Now, War-gamers/Simulationists have no problem with these weaknesses, and simply plan around them.  On the other hand, storygamers don't care for any rules, so this would be moot to them.

But, here I stand, as a cross between the wargamer and powergamer, and I can't help but think, "Why build a stronghold if it only exists to be attacked?" 

"But, the land around the stronghold generates revenue."  A pittance in comparison to what one dungeon delve could net.  And who is attacking the stronghold?  Orcs, bandits, barbarians, pirates, some lord's army...  Was there no warning?

A Shift

Let me back up for a second.  The kind of DM I'm talking about would say that there is a chance, a chance, that the stronghold could be attacked in our absence.  So, I ask, who?  Who is a potential threat?

 If Orcs, eliminate them.  If bandits or pirates, eliminate them.  If barbarians, eliminate them.  If some lord's army, eliminate them, take the baselard's head and put it on a pike outside the front gates.

 In no case should the players, or characters, be left without at least a possibility of being to do something, and...

You see what's happening, don't you?  The sphere of gameplay has changed, from dungeon-delving to domain-management.  But, where the key point lies is where it changed, the DM couldn't just tell the players "Hey, if you build a stronghold the game will shift to more of a domain based situation, y'know, kingdoms and lords, armies clashing and stuff," no.  

Again, the wargamers are entirely used to this, but the powergamers find it annoying.  To them, if you don't tell them what's happening, it feels like you stopped playing one game, and started playing another.  From this point of view, these are not two different fields of the same game, but different activities entirely.  It is a point of confusion.

There are two takeaways from this, the first is that, if powergamers are confused when shifting gameplay, storygamers become confused at any gameplay.

The second takeaway, is that, if there exists this shift in gameplay where strongholds are concerned, there also exists a shift in gameplay where treasure, and where henchmen are concerned.

 Henchmen

When the players, controlling their characters, first hire henchmen, a shift occurs in the playstyle, where, all of a sudden, you have a person you are responsible for, and who you do not directly control, aiding you in dungeon-delving.  I must repeat, the wargamer/simulationist will simply take this in stride, but the powergamer will feel a jarring effect on the gameplay, with no explanation given.

As a wargamer, I want henchmen to be people, with goals of their own, lives of their own.  As a powergamer, I want the henchmen to do their jobs, and not deviate from such.

The first understanding is as an investment, where the henchman, if treated well, and paid well, will be a great asset. 

The second understanding is as a piece of equipment, the henchman serves a purpose, and has no inherent reason to go against that purpose.

Each side is vehement and unyielding, and I... don't care.  This isn't what I play D&D for, I don't seek out some great moral truth from rolling dice, it isn't religion.

So, I have the henchmen do what they're told, exactly as they are told, until something goes horribly wrong, or the pay runs short, or maltreatment occurs.

I have the strongholds just work, until something goes horribly wrong, or if it isn't kept up for long enough, or if funds run dry.  

Speaking of funds...

 Treasure

 The same dilemma occurs, a similar shift in gameplay happens, and the responses are alike.  Treasure is the goal of the game, so why can it not just work? 

 Yes, it should be a burden to carry around the poundage that gold and silver entails.

Yes, with wealth comes responsibility, and a target on your back.

Yes, the market requires certain compensation to operate maximally.

 But, until the players and their characters do something bad, until they choose the wrong decision, everything that they own should operate normally.

And here is where the real difference is, when I run the game, the players will succeed so long as they do not make the wrong choices.

The Old-school dictates that the players should only succeed if they make all the right choices.

I ask you, which is more realistic?  Which is more cogent with your understanding of reality, and how the world works?

...

Should permanent progress be locked behind perfection?

...

The only morally correct thing to do when playing D&D is to have fun, because it is a game, and games are meant to be fun.

If you wanted to make this "moral quandary simulator" then you would be no better than those who want to make it therapy.  Or even worse those deviants who bring their freak**** into the game.  If you're doing any of this, then you aren't playing the game.

Be seeing you.