Time machine sizing, migration and brands

Three  sets of questions:
My main disk drive has 165GB used, of which about 1/2 is inactive.  (I never get around to deleting files, since the total disk size is 500GB.)  How big should my Time Machine be?
How should I migrate to a new  Time Machine?  Should I try to preserve old Time Machine data or start from scratch?
Any suggestions for Time Machine brands?

Tanks for the reply. Looks like I should get a 500GB time machine.  I still need help on:
How should I migrate to a new  Time Machine?  Should I try to preserve old Time Machine data or start from scratch?
Any suggestions for Time Machine brands?

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