When to Hold, When to Fold
Or rather, when you can trust your opponent to agree to a 1901 DMZ, and when do you just need to accept that you're going to have to bounce.
As always, the game is called Diplomacy not Tactics and there are always times when there are exceptions and exceptions to exceptions.
As the game progresses, any province in the game can be negotiated between players as zones of no-entry or a strategic bounce. A bounce can be a genuine move to keep each other out, a defensive move of allies to protect a third province between them, or a show of 'hey let's pretend to fight so other people think we aren't bosom buddies.' Or any other reason. So for the sake of this article we will look at the most common 1901 zones of contention and what you can reasonably expect form it.
Going from the Northwest corner and working clockwise and assuming that you genuinely want the DMZ or bounce in question:
1. The English Channel
The reason why you would both want it are obvious, but it's in both your interests (most of the time) not to move there, all else being equal. In case Russia moves north with Moscow, England usually wants two units touching Norway. France wants to ensure the Mid Atlantic in order to project into Iberia and set up his norther defenses. Neither want to antagonize the other into an alliance with Germany. If you set up a DMZ here, you can usually expect the other to hold by it.
Verdict: DMZ
2. Prussia and Silesia
Probably the 'safest' zone of contention on the entire map. Even if you never talk to each other, the odds Russia or Germany entering the zone is low. Not impossible, and new players tend to be more erratic than older hands, but there is usually little gain here. Warsaw on its own can't do much and even if Germany spends two of its three S01 turns moving on Warsaw, odds are very strong a Russian unit is in Ukraine or Moscow to help defend it. There are exceptions to this (Western Triple, a very daring Russia), but as a whole just sending a message to the other player asking for a DMZ will go down well and can be trusted.
Verdict: DMZ
3. Galicia
If (usually) Vienna gets into Galicia in S01, then the odds of Russia getting Rumania in 1901 dwindle. If Warsaw gets into Gal in S01, then Austria is extremely vulnerable to existential collapse, especially if Italy gets frisky too. A DMZ can work, but the incentive for both sides to break it, either to get the advantage for themselves or fear their enemy has the same idea.
In the fall it's not so bad, because then you get builds and Austria is almost certainly building in Austria or Budapest (or both), so the stab is less devastating and so is less likely to happen.
Verdict: Bounce in the spring, try to establish a DMZ in the fall.
4. Black Sea
For a decision that comes down to 'bounce or don't bounce in S01', this may be the most complicated one of all, bar possibly Venice-Trieste. For one, a 'bounce' here can mean a lot of things, ranging from all out war to attempting to cover up a Juggernaut. As a rule though, it is enormously advantageous if either party can get into Black in S01. But in true prisoner dilemma style, there are some very good reason for both sides not to go there. Turkey can try and get a second fleet out into Aegean faster. Russia can use to try and take Rumania in S01 and then bounce itself to keep Sev open in the fall. In short it's a lot less cut-and-dry than the three above cases.
It matters somewhat less in the Fall. Black Sea is always a great spot to be, but as a rule it's not worth Russia having two fleets in the Black Sea in order to get it. So in a prolonged war over it, it's increasingly likely to be Turkey's, as they are more likely to be able to devote the resources needed to win it.
Verdict: New players should probably set up a bounce in the spring, and Russians being content with that unless there's a really strong strategic reason to keep bouncing. A DMZ is almost certainly going to be broken unless you've agreed to a serious long-term commitment to each other, akin to a Juggernaut.
5. Bohemia-Tyrolia-Trieste-Venice
The rest is tricky. A bounce could mean war or it could mean a hold but let's order something other than hold just because. Trieste may attack Venice with no intention of keeping it, but as a preventative measure to prevent Venice to Tyrolia in conjunction with Rome to Venice. In fact unless you are trying to capture Greece, this is what Trieste should do every time, no matter how friendly you are with Italy. Venice can use the same logic to break up (the much much much much approaching 0% in practice) less likely move set of Trieste to Adriatic and Vienna or Budapest to Trieste. Or it could do it to try and just walk in.
This is complicated by the fact that Germany probably approves of a DMZ in Tyr, but everyone knows he doesn't have the teeth in S01 to really do anything about it if the DMZ is violated.
You just have to go with your gut and reading of the board and the players on this one, there's so many options it's impossible to say there's a right one. Personally I always figure I'll go for Greece every time and worry about the ramifications of Italy moving to Trieste later (and diplomatically I always try to get him onside). I always try to get Germany to request a DMZ in Tyrolia, which I just so happen to always agree to when he offers it to me and Italy. As Italy it will depend on what alliances you can make, because you're thought is always going to be 'what do I grab after Tunis'. If an ally provides a concrete answer, great. If not, and Trieste is just sitting there...
Verdict: No Verdict
6. Piedmont
Given Italy's complications on the other side of Venice, it's no surprise that most Italians are happy with a DMZ in Piedmont. Not like they can do anything with it anyway with just an army. And France has more pressing matters. That said, because the expectation of Italy going there is so low, if done right it has a chance of devastating effectiveness, either pushing into Marseille itself or forcing France to lose out on a 1901 Iberia dot in favor of running home (and subsequently preventing any build in Marseille itself). If you bluff and France calls it or you end up bouncing and thus leaving Marseille open for a build AND France getting Spain, he's likely going to hit you back hard. There's a reason this move is done so rarely.
Verdict: DMZ, but watch your back just in case.
7. Burgundy
When I first started playing Diplomacy, Burgundy was treated as a slightly-French neutral territory where an arranged bounce between Paris and Munich was the polite thing to do and France supporting himself into Burgundy was basically a declaration of war. Nowadays, Burgundy is generally viewed as an integral part of France and while a supported move to Burgundy is viewed in Berlin with some concern, it is not necessarily outright alarm. I add more for completion sake, but while France and Germany may discuss Burgundy, I don't believe it is at the level where there is any real question of France's right to move there. A bounce may be arranged, but it's not anywhere near the level of strategic obligation as clarifying (or maintaining strategic silence) about the Channel or Black Sea or Tyrolia.
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