Overall, not that many. The worst time and place to be a bomber pilot (or crewman) was in early 1943 in England as a member of the 8th Air Force, engaged in the strategic bombing of Europe (which in 1943 meant almost entirely raids on occupied France). This was before belly "drop tanks" became common and long range fighter escort planes were in theater, so the bombers had to penetrate enemy air space unescorted and suffered heavy losses. The US had begun its daylight strategic bombing in Europr in August 1942 with a tiny force. A "tour of duty" meant completing 25 missions, and the crew of the B-17 "Memphis Belle" was the first to do so in May 1943, and at that time this was truly defying the odds and walking on water. But by late 1943 early-1944 there were hundreds more US bombers on the raids, the escort fighters could now go much deeper, and the German Air Force was suffering from attrition, so it got much less deadly for US bomber pilots in Europe as time went on. Overall, there were 16 million Americans in uniform in WWII, and 2 million of these served in the 8th AF bombing Europe from England. Of that 2 million, only 27,000 were killed in action. Of course, only a small percentage of that 2 million was combat crews. Bomber pilots in other commands could also face tough missions, but in general the "big leagues" were the 8th AF in England. There was also the 9th AF in England, flying medium bombers on tactical missions, and the 12th AF in Italy flying heavy bombers on strategic raids into southern Germany. There were the 14th and 20 AFs in the Pacific bombing Japan. By FAR, far and away, the most deadly job in WWII was being a foot soldier, a rifleman in a rifle platoon on the front lines. The vast majority of US KIA were riflemen. And being a rifle platoon leader was the deadliest job of all. The US WWII military (and its still true today) had a massive "logistical tail" with dozens of men behind the lines for every one in combat. There were never very many riflemen, sometimes nowhere near enough, and in some units the average position had to be replaced ten times.
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Tank crewman, infantrymen, sailors, artillerymen, etc. can be trained in 8 to 16 weeks. It takes years to train top notch military pilots. The Battle of Midway took away the "cream of the crop" of their combat pilots and air crewmen (fighter pilots, dive bomber pilots and rear gunners, torpedo bomber pilots and gunners and torpedomen). Japan should have trained more pilots than it did. But apparently, Japan did not think that they would lose so many pilots during the war. From Midway afterwards, for the most part, inexperienced (naval) pilots would be fighting against the US and it's allies.
Not counting helicoper pilots and aircrewmen; over 6,000 Fixed-wing/propeller/jet US pilots and aircrewmen were killed or missing during the Vietnam War.
There were 98 American aircraft destroyed (it may include planes destroyed on the ground at Midway), though not all there pilots were killed. The figure of 307 includes aircraft crewmen (non-pilots) losses on the island of Midway and people assigned to ships crews.
This Question is impossible to answer. There were probably thousands of B-29 pilots and the Army (Air Force) did not keep a roster of every one. Also the pilots were in many different units: bomber units, training units. If you knew of one specific unit, then you may be able to obtain a roster of that unit for a specific date.
During WW2, the Germans developed a guided missile that was dropped from a bomber. It used a TV camera. The bomb was called the Fritz. Link: http://www.ausairpower.net/WW2-PGMs.html The Americans tried to develope a guided bomber that used TV's. A B-24 was converted so it could be remotely controlled. Pilots were used to fly the aircraft from the airport and after gaining altitude and correct heading, they would bail out. This program was canceled when one blew up in flight and killed Joe Kennedy, the future President Kennedy's brother.