Alright -- So I have an update and a few questions.
I went ahead and wired up a single-LED-circuit to test forward voltage deviation between the LEDS I have purchased. While doing so I noticed that I can run a single LED (3.3V forward voltage) with a 660ohm resistor. This provides the LED with 2.6ma of current. Even with such a lower amount of current the LED is plenty bright enough for what I need.
With this being said -- It's occurred to me that 8 LEDS in parallel running at 2.5ma would equal 20ma.
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Would it be safe to run these LEDs in parallel since maximum current draw will be 20ma (safe for even a single LED)?
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If so, could I simply create 8-LED segments in parallel and power them from a single port on a MAX7219?
If so that would be great and would eliminate several problems!