1st or 2nd

Question: You got a trophy that was two feet tall and your friend got a trophy that was 1 yard tall. Did you get 1st or 2nd?

Question: When is 99 more than 100?

Question: You have a glass of water that looks about half full. How can you tell, only using the glass of water itself, if the glass is half full or not?

The glass is a right cylinder.

Question: There is a 5 gallon and a 3 gallon box. You also have a hose with unlimited water. How are you gonna make the 5 gallon have 4 gallons using your items? (You do not know the exact measure measurements of a gallon)

Question: Hard, Harder, and Hardest are brothers. By age from youngest to oldest, it goes Hard, Harder, Hardest. Hard is half the age of Hardest who is 20 which means hard is 10. Harder has a two-year difference between the number of years older he is than Hard and the number of years younger he is than Hardest. Harder is closer to the age of Hard than Hardest. How old is Harder?

Question: What are the next two letters in the following series and why? WATNTLITFS__