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Hi Ed, sounds like you have accumulated quite a collection of eyepieces already in your 2 short years!
A lot of experienced observers will tend to spend most of their observing time in a session using one or two premium eyepieces suited to the conditions. The sweet spot is often around about 4mm exit pupil, so for me with my current scope, the most used EP is the 20mm Nagler T5 (exit pupil of 4mm without Paracorr, 3.5mm with Paracorr).
If the budget for premium eyepieces is limited, then in addition to the 4mm exit pupil EP, you might get a premium eyepiece at about 2- 2.5mm (in my case that is a 13mm Ethos) and another between 5-6mm (for me, a 31mm Nagler). I am currently planning to sell my 20 Nagler in favour of a 21 Ethos to really smash that sweet spot!
I have heard others talk in terms an array built around exit pupils of 1mm/3mm/5mm as an alternative.
Buying and discussing EPs is part of the fun of observing. The truth is that most of us end up with many more than three premium EPs. It is nice to have options for moments of really good seeing, or just comparing the same object through a range of difference EPs to appreciate different features.
If I can add any light to your thinking it would probably be to sell most of your current entry level eyepieces and pool the money together to get a few top shelf ones. Hope that helps.
Cheers!
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