How much eye relief do you need?
I agree with your thoughts in that in my opinon it is more enjoyable to have 2-3 really high quality eyepieces and use them often.
Televue has some really helpful suggestions as to good magnification ranges on their site
http://www.televue.com/engine/page.asp?ID=221
If you have not read through the other material on the site it is worth a read...of course their choices will point you toward TV but that aside I found it a good source of eyepiece terms and philosophy...
As you know (or will learn soon) Maximum FOV will come with the Ethos eyepieces (there is also the Explore Scientific range of new 100 degree FOV at a lower price...they are good by user accounts but not quite in the Ethos league although some may be hard pressed to see the difference)
Lighter weight will be the Nagler T6 series (I've owned/used the 13 and 11 to very good effect)...but some feel that eye relief (15 mm I think) is a smidge too short to use them with glasses)...
Fun challenge...