#1
Does it matter what order i put plugins into the track in my DAW, e.g. if i add compressions then reverb would it be different than putting in reverb then compression
#2
Yes.

If you put reverb in first then you will be compressing both the dry and reverb'd signal.

Putting the compressor in first means you'll only compress the dry signal and the reverb will be applied to the compressed signal.
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#3
it absolutely matters, just as if you had gear cabled up in the studio
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