You say that all of your music is on your Mac. Is it all in one library, or do you have separate iTunes libraries.
If they are separate then it will be complicated, as using one iTunes match account will result in all the libraries being made available, which could be quite messy.
If the music is all in one iTunes library then it is quite easy. Just sign up to Match on your Mac and let it get on with matching and uploading to the cloud. Then turn match on on each persons devices. There is a limit of 10 devices which can be used, and the Mac is counted as one of them.
If you have individual iCloud accounts then that won't affect things as it is a separate thing, but if you have different iTunes accounts that you purchase music on then this may cause some problems with matching, as songs only show up as purchased if they were bought on the same iTunes account as that which you use to sign up to Match.
Hope that makes sense.