Maybe it is because of the type of Tea leaves I am used to (black tea), and the fact that I often have milk as well, I would say the first time tastes the best for me.

Do you let it steep longer the second and third time?

#2 most of the times but not always. Japanese green teas is normally an ecception because you pour the Tea directly the second and third time. But with oolong and pu-erh I have the brewing scheduale. First time 30 sek, second time 1 min, third time 1,5 min, fourth time 2 min, fifth time 3 min, sixth time 5 min, seventh time 7 min, eigths time (rare) 10 min, ninth time 15 min etc

Wow, that's serious.

I'm the same as Jordan, I never even think to reuse my Tea.