(2) Which major powers to declare war on, when, and any associated conditions concerning same.
For the CW, this is a set of decisions that (thankfully) does not often have to get made, since in most scenarios it's already at war with most or all of its opponents. To whit:
Germany: The CW begins every WiF scenario it appears in either declaring war upon or already at war with Germany from the get-go. Easy enough.
Italy: The CW has to make a decision about war with Italy in the following scenarios: Fascist Tide (1939 2-map) and Global War (1939). It is at war with Italy in all other scenarios.
Japan: The CW has to make a decision about war with Japan in the Global War, Missed the Bus, and Lebensraum campaigns. It may have to make a decision in the Waking Giant campaign and the Day of Infamy 2-map scenario if the Japanese player (mysteriously) doesn't declare war. It is at war with Japan in all other scenarios those two powers appear in.
There should be a reasonable way of formulating a general process by which CW, or any other power for that matter, chooses to declare war on another one.
Balance of Forces
What is CW's balance of forces vs. Italy or Japan? The overall picture would range along some kind of axis, from Extremely Unfavourable to Extremely Favourable to somewhere in between. The balance of forces would be defined by a number of sub-properties, some of which I will list here.
Absolute number of units: Quantity is its own quality. The more units of each type the CW has than Italy or Japan do in the potential theatre of conflict, the more favourable things are for the CW, and vice-versa.
Quality of units: Who has more white-print units? Who has more combat factors? Who has better air units? Who has better naval units?
Nature and positioning of units: Are the CW's units in theatre a bunch of ARM/MECH stuffed against the Libyan border or MAR/PARA sitting in Rabaul waiting to be deployed? Or are they GARR, MIL, positioned on key garrison cities.
Logistics: How easy is it for the CW to keep its forces in supply? How easy is it for Italy or Japan, in the event that the CW goes to war with them, to do the same?
Reinforcements: How much additional force can the CW bring in to the theatre once the war begins, & how much can Italy or Japan bring in?
Short-Term Consequences of CW DoW
What are the expected short-term military & political consequences of a CW DoW (that is, during the surprise impulse & the rest of the turn that the war begins in)? Once again, an axis along which Least Favourable to Most Favourable consequences appears, with discrete points in between at presumably regular intervals.
Destruction of Enemy Materiél: How much damage can the CW inflict during the surprise impulse, and what sort of units is it destroying anyway?
Territorial Gains: How much territory, especially resource & victory hexes, will the CW gain during the surprise impulse & the rest of the turn?
Expected Losses: What does the CW expect to lose in the surprise impulse & the rest of the turn?
US Entry: Can the US entry pool handle the worst-case chit loss?
Long-Term Consequences of CW DoW
What are the long-term military & political consequences of a CW declaration of war on Italy or Japan rather than vice-versa?
Commitment to Theatre: How much commitment will this theatre demand from the CW if it goes on the attack right away? Can it afford to meet that commitment over time?
Protracted Contests: Can the CW's forces in place handle fighting a long-fought contest over the sea areas & land regions in the theatre under consideration? If they can't, what additional forces are needed to allow them to do so?
Long-Term US Entry: By declaring war and taking away US entry chits, what delay will the CW inflict upon the selection of key US entry options, and more importantly how long will US entry into the war be delayed? For this section, the average values of chits in each year comes into play.
Consequences of Reverse Situation
While of course the CW may be declaring war upon Italy or Japan because it believes it has a better balance of forces, can inflict damage and take turf in the short run, and tough it out for the long run, sometimes the CW will consider declaring war on them just to keep them from getting a surprise impulse on it. So, the CW will want to analyse the situation as much as it can from the standpoint of Italy or Japan, using all the above considerations, and decide if it is in their favour to declare war soon on the CW.
The more critical the surprise impulse Japan or Italy will get if they declare war compared to the rest of the struggle, the more likely the CW will want to pre-empt them.
Likely Results
Taking all the latter into account, I think that the CW has a reasonable chance of declaring war on Italy anytime in 1939-1940, and it will depend on what can be made of the surprise impulse. By contrast, the CW will probably not be even close to declaring war on Japan until some time in 1942, by which point it is almost certainly moot since Japan will most likely have declared war on the CW.