Ok Zavek, let’s take a look…
So for more damage, you’re basically looking at both weapons, both rings, and your amulet. Your gloves are quads already and although they are not perfect, I would not specifically target getting a new pair at this point.
300th Spear- Could pick up 4.6% damage from higher damage roll, and 7.5% damage from higher affix roll, plus about 100 more STR, which should be about a 1% gain for you right now, that’s a total of about 13.6% damage you could gain there.
Arreat’s Law- Here, you could pick up 1.8% damage from a higher damage roll. That’s assuming you get a primal without damage %. An extra ~150 STR there would be about 1.5% more damage. And picking up 10% CDR would get you 2.8% straight damage via Crimson, plus better cooldowns of course.
For some reason I can’t see the affix roll on your Arreat’s, but it’s easy to figure out the value of a gain there yourself. You just have to remember to add in an extra 100% “base” damage on both sides of the equation. For instance, if your current one was the same as your 300th and had a 179% roll, then getting a perfect roll there would give you a gain of 3.00 / 2.79 = 1.075 = +7.5%.
So on your Arreat’s, a perfect one would gain you 6.2% damage, plus whatever you could gain on your affix.
Band of Might- a perfect BoM with CHC/CHD/Damage Range would gain you about 7.6% damage from CHC and CHD, and another 7.6% from the Damage Range, though this would cost you a little CDR, so let’s call it maybe 4% net for that roll. So that’s about 12% total damage you stand to gain there.
Compass Rose- getting to perfect CHC/CHD/Damage Range here would gain you about 3.2% damage from CHC and CHD, and again about 4% net for Damage Range since you gain some damage but lose a little too from lost CDR. So that’s only about 7.3% total damage you could gain here.
Traveler’s Pledge- Getting a perfect roll of Physical%/CHC/CHD would gain you 16.7% from the extra elemental % but also cost you about 10% damage from lost Str. So that’s an actual gain of about 6%.
So I’m not entirely sure about your Arreat’s since I can’t see the affix, but the upgrade priority is probably:
300th > Arreat’s > BoM > Compass > Pledge