Long story short, I created an Excel sheet to perform some ratio calculations and had issues, so I posted the question on the computer/programming section which deviated a bit towards this thread.
So I'm somewhat ceasing that thread as the Excel question got answered and now I remain baffled at why my drill press is so far off when I measure the speeds with a meter.
The attached are the measurements I got, the belt setting, and the speed it should be from the plate on the drill press.
My initial desire was to buy a secondary pulley and/or figure out if I can drive directly from the motor to the chuck and get the middle speeds (1000/1100/1200), however, now I'm finding that maybe someone replaced a pulley since my numbers are far off.
Also, I know some replace the motor with a three-phase and use a knob, but my goal is more or less understanding how to calculate the ratios correctly, correctly measure the pulleys, and find out just what someone may have done to get these numbers so far off.
If I didn't mention it already, my motor speed (according to my meter) is 1777RPMs.
One other thing is that I used an elastic band to drive the motor and idler to eliminate the pitch diameter of the belt. These numbers I have written somewhere, but believe the lower speeds were close to my idler calculated, but the higher speeds were grossly off (much higher).