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As to the eyepiece query, I'll give the lawyers answer, it all depends!
Generally you will use your low power ones the most. Ther are hundreds of objects that look fantastic at low power (eg less than 100x).
If I assume your 8" dob as an f6, it has a focal length of 1200mm. If you have the standard eyepieces you will have a 25mm giving 48x and a 10mm giving 120x. At 48x many objects like M42, M43, Omega Centauri, 47 Tuc, Eta Carina neb will look great. The higher power will often not help.
THe high power EP can be used if you want to get the Homonculus around Eta Car, get closer view of Saturn. Jupiter is just about done for this year. I got almost all the Messiers using an 8" dob and 25mm EP.
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