Question:
Does it matter what order I add the FX plugins in Cakewalk?
Not really. It depends on where you want to go today.
If you want to emphasize a frequency range i.e. make it stand out, you will run the EQ prior to compression and turn up the range you want to stand out. Compressors tend to bring to the front the most dominate (loudest) frequencies in the signal.
If you want to control the color a compressor adds to the signal, you will EQ after the compressor. Lets say the compressor is bringing out the high end clickiness of bass guitar strings. You might want to EQ after the fact to reduce that range and give the bass a more low dominate sound. Or, just the opposite can occur where too much low end is coming out of the compressor.
Reverb should generally be set out on an aux buss and mixed back in with the main or unaffected signal. This is not mandatory however. If I need to EQ the vocal in the mix I put one plug in EQ on the main vocal or instrument track (It's better to track the correct EQ though) I will then send any special effects I need to an aux bus with the plug ins i.e reverb, flange, phase, delay.
If I do not like the native sound of the special effects I may place an EQ either before or after the special effects chain so I can focus in a just a specific range of a vocal or instrument to be effected. This is especially useful for vocals with reverb or delay. By focusing on specific frequency ranges you can really clean up a sloppy reverb or delay that is clouding the mix.
Same with drums. A common technique is to zero in on a specific part of the snare, toms and cymbals to control the reverb sound and give the effect that they are in a big room. You control what frequencies come out of reverb or delay and make sure they are not conflicting with the part of the vocal signal coming out of their own reverb/delay. Keeps the mix clean sounding and in control.
All this holds true unless you are going for that garage band sound. Then just turn it up to 10 and hit record. Just kidding of course, even garage bands need a vocal to sit up front.