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I upgraded over the past few years and now have a set I'm happy with. I have two types of eyepiece: ultra wide angle for deep sky and orthos for planets and moon. The wides they are in a series with a ratio of about 3:2 between sizes 28, 20, 13 and 9. The smaller three are all Naglers and the 28 is the WO UWAN. I haven't compared the WO to a Nagler of similar size but judging it next to the 20mm Nagler suggests it is very good. The orthos are a Zeiss Jana 10mm and 7 & 5mm UO HDs. Nothing I've seen can match orthos for sharpness and contrast - and the UOs are pretty cheap.
Of these eps only the 13, 7 and 5 were bought new; the rest were second hand here on IIS. The trick is to know what you want and why then check the classifieds at least daily. If it's worth having it will go very quickly. (BTW it seems to me that there is less good stuff coming up at the moment.) When planning a 'budget' I kept in mind that good eps will last forever (well longer than me anyway) and since the expenditure was spaced out over 2+ years the pain wasn't too great.
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