The better chance...

Who had the better chance of winning their respective war, the German Imperial Army of WWI, or the German Wehrmacht of WWII?

I'm going to tentatively say the Kaiser had a better chance (although both wars looked pretty lost when they hit their greatest extent)...
Here's why:

1). The Bundeswehr Was Stronger: The Wehrmacht started off in a much weaker position than the Bundeswehr due to several factors. Germany had lost a large number of its adult male pops in the last war. The Versailles Treaty limited their military capability for most of the Interwar period while Britain and France spent those years building defenses. In 1939, Germany had only 78 divisions versus France's 86 and Poland's 43. Morale at the beginning (right up until France went down) wasn't great due to the memories of the last war and knowledge of the above. The Blitzkrieg tactics? Those were developed because Poland and France had to go down quickly. The Wehrmacht just couldn't afford anything less than a lightning-speed victory. Hitler had to use almost the entire Heer in Poland and got very worried when Poland took longer than anticipated to capitulate. Compare this to the German Empire, which had undoubtedly the most powerful army in the world in 1914.

2). The Nazis Were in a Better Diplomatic Position But Squandered It: By this I mean it probably wasn't guaranteed that Hitler would be fighting Russia and the Western Allies at the same time. It's difficult to overestimate the importance of the Molotov-Ribbentrop Pact. Since Russians had done most of the dying in the last war, the Allies wanted them back in the fight. The Pact thus wrecked their morale and came as a great shock. Hitler could freely invade the Soviets whenever he felt like. His mistake? Invading while the Brits were still in the fight, thus guaranteeing him another fight on two fronts. Honestly though, this point most leads us into the next one...

3). Hitler Had the Instincts of a Meth Addict: And he wouldn't stop meddling in the Wehrmacht's business. I'll happily argue that Hitler was a pretty darn good politician, but the man made some truly baffling mistakes. Like making the Luftwaffe target British cities instead of taking out the RAF. Or the "no retreating ever" policy. Or cancelling weapons research after the Fall of France. Or delaying his push on Moscow to send his panzers south. Or using the Me-262 as a freakin' bomber instead of a fighter. Or diverting vital resources for the pointless murder of undesirables. Or spreading his armies too thin between Stalingrad and the Caucasus. Or ordering a doomed attack on the Kursk salient. The Wehrmacht was the most effective fighting force in the world, but they were constantly limited by their leader's stupidity.

4). The Kaiser had a Better Navy: This one is kinda self-explanatory. If they fought intelligently, the Germans could be a real headache for the Royal Navy. Meanwhile Hitler had to rely on his Wolfpacks, especially after he decided to scrap his surface fleet for no reason.

5). Hitler Had Stronger Enemies: The Wehrmacht looked pretty good taking out a bunch of nations that didn't see them coming, but after that, they were fighting immensely powerful foes. The USSR put up a very spirited fight, especially their partisan forces, and their industrial capacity was enormous. Meanwhile, they had the USA in the West, which managed to help the UK liberate France while using a fraction of their potential strength. The USA had more than half of the world's industrial capacity at the time and happily supplied the other two combatants with weapons and materiel. The difference in the First World War was, the Kaiser was fighting a weaker Russia and had a real chance of keeping the USA out of the war. For this reason, the situation in 1944 was much more hopeless for Germany than the situation in 1918.

6). The Kaiser Had Better Opportunities: The relative strengths of the two Germanies can be illustrated with alternate history. There are plenty of alt history scenarios which could have seen a pretty decent chance for Imperial victory. What if they went with an eastern strategy? What if they won a few key (narrowly lost) battles in France and took Paris? What if they didn't draw in the Americans? Meanwhile, most alt hist scenarios about the Nazis boil down to "how many Russians can we kill before we get steamrolled?"

7). The Kaiser Had More Flexible and Realistic Wargoals: Honestly, there are any number of conditions which can be described as Germany "winning" the First World War. Perhaps (probably) there could have been a negotiated settlement acknowledging German gains in the east. Beyond certain colonial concessions, Germany really didn't see any reason to threaten Britain and France's core interests, and those colonial concessions would likely have been quite limited. All this truly required was successfully keeping the front lines inside France's borders. Meanwhile a Nazi victory required the total conquest of the Soviet Union and a victory over the Western Allies. Both were completely impossible.

5). Hitler Had Stronger Enemies: The Wehrmacht looked pretty good taking out a bunch of nations that didn't see them coming, but after that, they were fighting immensely powerful foes.

Yes. 100%.

Churchill definitely regarded Germany's relative position as stronger in the First World War than in the Second.

German U-boats enjoyed greater success before the invention of Sonar. If memory serves, they actually sank more tons of shipping in the First War.

I've also read that, despite being outnumbered, German aerial forces remained tactically equivalent to the combined American, British and French aerial forces right up until the end of the war due to the development and successful mass production of superior aircraft. Some of Germany's air machines were also superior during the 2nd World War, but not by enough to counterbalance the horrific odds they faced going up against the US Army Air Corps from late 1942 to the end of the war.

Thorfinn Karlsefni wrote: Some of Germany's air machines were also superior during the 2nd World War, but not by enough to counterbalance the horrific odds they faced going up against the US Army Air Corps from late 1942 to the end of the war.

That makes me think again of the Me-262. It was the world's first jet interceptor and was easily at least 5-10 years ahead of its time. It had a cruising speed of 460mph and a top speed of about 540mph. Its range was approximately 650 miles, and its ceiling was 38,000 feet. It was better than anything the Allies had, and it could shoot down planes with inpunity. The real threat was the rockets, which they would fire to break up formations, quickly moving in to pick off anything left. Sadly for the Nazis (and thankfully for everyone else), it never saw extensive action until the last year of the war, and never in groups of more than 50-60.

And that is why I mentioned that plane in point 3: Hitler was an Idiot.

Here's an excerpt from an article by Defense Media Network:

DMF wrote:Revisionist histories often downplay Hitler‘s role in sabotaging the Me 262 by demanding that it be used as a “blitz bomber” against Allied ground troops, rather than as an air-to-air fighter to sweep the skies clean of Allied warplanes that were swarming over the Reich. During the Insterburg demonstration, the Fuehrer asked whether his new jet could carry bombs and was told that it could. What Hitler’s lapdogs didn’t say was that extensive modifications would be required and that experienced Luftwaffe combat leaders believed they could achieve more in the air-to-air role.

“I’ll never change an opinion I’ve expressed often, that with just 300 Messerschmitt Me 262 jet fighters we could have on any day shot down a minimum of 200 bombers,” said Galland. “If this could have continued for even a fortnight, then the day bombing would have had to be halted.” Galland called the “blitz bomber” idea “a typical Hitler error.”

To be fair to the man, that was partly based on how the plane's builders sold it to him, but he really should have known better. It ended up being a predictable failure, because precision bombing was hard enough back then even when you weren't zipping around at 500 miles per hour. They ended up slowing down production to modify the plane into a bomber, then slowed it down again to go back to the interceptor design. By then it was way too late.