Hi Matt,
Both Adrian and Suzy have given some great info, and there's such a wealth of experience here on this forum you're sure to find the right answers...I just thought I'd mention my own experience with a premium eyepiece. I bought a 13mm Nagler for my 8" dob, and it's pretty much all I use, combined with a 2x barlow. I haven't looked through other premium eyepieces, so I can't compare it to other eyepieces, but all I can say is it's worth every cent I paid. The views are wonderful, the contrast is amazing and my whole observing experience has become so much richer.
I'm hoping to get a longer f/l eyepiece in the future, but at the moment I can quite happily spend a whole evening with just the one eyepiece + barlow. I don't know for sure, but I imagine any eyepiece of very good to excellent quality would provide a similar experience. One thing I do know is how much more I enjoy time at the telescope with one great eyepiece rather than 3 or 4 average to good ones.
Just my own (rather limited!) experience.....
Cheers
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