1. Yes! definitely need to adjust the steps per mm for the extruder. Solidoodle sets it FAR to high. should be more like 102-105 vs the 138 they have it set at.
Measure and mark 100mms on the filament feeding into the extruder top (you may want to make a second mark at 150mms). in RH free extrude 100mms - measure how much it fed past the 100mm mark (or how much remains to the 150mm mark)
use this formula to calculate the corrected steps/mm:
(expected length* x current steps per mm) / actual length = new steps per mm.
*expected length is the 100mm you asked for
2. If you are using the stock hotend, then yes, the fan on the side is necessary to keep the cool side of the hotend cool enough to prevent heat-creep and internal meltdown of the PEEK liner. If you upgrade the hotend to an all metal like the E3D v6, then it could be removed.
3. I have no experience flashing the Printrboard, so cant really comment on that one, but i see no reason why you couldn't. Others here have more experience with this.
SD4 #1 & #2 - Lawsy carriages, E3D v6, Rumba controller board, mirror bed plate, X motor fan, upgraded PSU & Mica bed heater
SD4 #3 - in the works ~ Folgertech FT-5, rev 1
Printit Industries Beta Tester - Horizon H1