I am sorry, but I can't see any way of solving this, I can only make a schedule for 1 month. By the way, I count 15 opponents per person per month, so I don't see that there is an issue about 'twice in the same month'. If it helps here is my 1 month schedule.
Machine 1 Machine 2 Machine 3 Machine 4 Machine 5 Bye
(11 20 15 2) (23 6 12 14) (17 21 1 8) (18 19 7 3) (5 16 24 10) (22 9 4 13)
(12 21 16 3) (24 1 7 15) (18 22 2 9) (13 20 8 4) (6 17 19 11) (23 10 5 14)
( 7 22 17 4) (19 2 8 16) (13 23 3 10) (14 21 9 5) (1 18 20 12) (24 11 6 15)
( 8 23 18 5) (20 3 9 17) (14 24 4 11) (15 22 10 6) (2 13 21 7) (19 12 1 16)
( 9 24 13 6) (21 4 10 18) (15 19 5 12) (16 23 11 1) (3 14 22 8) (20 7 2 17)
(10 19 14 1) (22 5 11 13) (16 20 6 7) (17 24 12 2) (4 15 23 9) (21 8 3 18)
Because of the way it is constructed, with groups of players (1 2 3 4 5 6), (7 8 9 10 11 12), etc. in the columns, members of the same group can not play each other without violating the 4th criterion above.