I guess I'll have to get more specific on the next clue since I'm running out of clues.
Looking for a pilot in this case
1) This aviation pioneer was self taught
2) He made history less than a year after learning to fly
3) He was killed in a crash less than a year later
4) He was posthumously awarded a flying medal for the feats he previously performed
5) In his first "history making" flight, he actually damaged his plane
6) His flight lasted only 2.5 miles
7) He fatally crashed in the southeastern part of his home country
8) His fatal crash was only two days short of his 25th birthday
9) During his "history making" flights, he and his plane both were equipped with flotation since part of the flights were over water
10) Between two of his flights, he had a meal with a high ranking military officer
11) This person NEVER flew a combat mission
12) This person NEVER served in the military
13) This person flew a plane that was built by another aviation pioneer's company during his "history making" flights
14) This person's flights indirectly led to an innovation in another country during a major conflict a few years later
15) The innovation referred to in clue 14 is still having a major affect on world politics and the military strategy of countries that use it, 100 years later
16) This person had no contact, that I know of anyway, with the Wright Brothers or their planes
17) He was awarded his flying award, a DFC, 21 years after his fatal crash
18) The "history making" flights involved a city and an unrelated state
19) The runways for these flights had to be specially made just for the flights to be possible
Good Luck