Hey Drew,
The good thing is that eyepieces you accumulate you keep along the way.
It depends on what you like and willing to pay for it. Genereally the wider the view(degrees like 82 and above) and the longer focal length eyepieces cost more.
If you can wait, i know from experience this is hard, you can get savings by buying second hand. Eyepieces do hold their value.
I reckon for myself, i have gotten value out of the eyepieces I have and I am happy. Trying different eyepieces is an expensive excercise
M11