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Keep in mind that some of the info may be dated, but in general I believe it to be fairly accurate still as far as a general guide to follow.
Would recommend 5, 6, & 7, but definitely not 8 from your list. -20% monster costs is not going to give you the types of returns some of those other things will. However, I would definitely start with the Hell upgrades outlined in the link I included.
At the end of the day: Play it your way because you'll get so many opinions that it may become confusing.
Arcane Lab - If you are playing reasonably actively then this is letting you add more and more items that boost you rather than being just a one off boost.
Imitation Orb Shard - gives you twice as many orbs, and doubles the speed you unlock the x5 dps, x5 skulls (and more x2 white orbs) via the white orb achievements
Carl's Toenails - x9 DPS and improves later as you clear more realms
Bank/Armory - x5 to about x9 DPS or skulls, although as they get more expensive (1000 diamonds) probably do the next couple before returning to the later levels
Xmas Warhammer - x3 DPS
Carl's Birthday Card - +25% or so white orbs currently for you, but every realm you progress this makes less different (+20% when you reach the x5 time portals, +16.667% when you reach x6, and so on)
Golden Shower - +33% to click dps only, not a major boost but it is cheap at least (compared to most things at this point)
Steve the Xmas Star - -20% cost is equivalent to +25% skulls, so it will be a long time before this is the best thing to do with diamonds
It seems to be a bug, happens every now and then when skulls are in flight while you are resetting I think - a common time it happens is after killing wizards in my experience.