Can I make two lots of hay?

Waikato based, have got about 9 productive acres, stocked with 8 x 90kg weaners. About a fortnight ago had hay made from two of the paddocks. Currently the weaners are in a long (about 400 metre driveway) which has about 12 feet of good grass on each side. For the next few months I intend to rotate the weaners between the driveway and 2 other paddocks of about 1.5 acres each. The "big" paddock of about 5 acres I was going to let grow and get hay made again in Jan/Feb hopefully by a contractor who does everything and just pays $20 per large round bale. My questions are;

Am I mad?

Am I sensible?

Will anybody want to make hay in Jan/Feb?

Will my grass grow OK once cut in Jan/Feb (Waikato weather)?

Any suggestions/advice much appreciated.