Give it a try and i'll give you some advices.

When you're playing as Tryndamere you sould be agressive but beware ganks at low level at higher level too but not too mutch and maintain a distance from the bushes.At middle level you sould have a good score and you can start press the atack and get a nice score but make shure you're always protected cause you at higger level will get a awesome lifesteal. At higher level you can solo 2 or 3 champions by yourself but don't get to excited cause you may die sometimes But make sure that you have your ulti ready to be used for an emergency.

Give it a try It will give Nice Damage And Lifesteal and Nice Battle Histories :D. Good Luck!!