Schwaggy Bud - $15-20 per 8th, $80-100 per O
Good Regs (usually non-compressed/bricked and coated with crystal) - $20 per 8th, $100-120 per O
Good Mids (sometimes rivals the quality of chron, never compressed/bricked) - $30 per 8th, $150 per O
Sometimes I can get decent, better-than-mids quality seedless bud for around $40 an 8th, $200-275 per O, but it's rare, so...
Chron (Dro/Headies/Dank/Whatever) - $50-60 an 8th, ounce prices vary, but usually in the $350-450 range for the good stuff, $375 seems to be a common price
I used to have a guy who sold almost nothing but name brand strains (Mr. Nice Guy, Neon Kush, NYC Diesel, Sour Diesel, and a lot of others), but honestly, his stuff only looked/smelled/tasted the best. The best highs I've ever gotten have been from no-name generic chronic. The stuff that goes for $60 an 8th around here is always name-brand quality. $50 an 8th bud varies, but it's usually damn good. There are a couple of sellers who insist on charging $20/gram ($70 an 8th) with no discounts for some of their top name-brand stuff, but it's never any better than what I can get for $60 an 8th (and usually no better than what I could get for $50), so I only go to those guys on rare desperate occasions. The "regs" I get for $20 an 8th are amazingly good compared to the bud I've ever seen anyone else get for that price, and honestly sometimes get me as high or higher than chron.
And sorry for the ranting and whatnot. This post is heavily weed-driven and partially acid-driven, although that's mostly gone now.