maepartner....this is really two questions.
1. Two different use months. Some have said this is a hassle, many others have said it's no problem. I think I fall into the "it's no big deal" group if you are somewhat organized. You have two different banking deadlines to worry about, but it isn't like it requires daily effort.
2. Two small or one large contract. I've seen the advice here, and it makes sense to me, that two smaller contracts is a preferable situation to one large one. Why? If you have two kids (or other beneficiaries) you can give one to each...you cannot split the large contract. Also, if you wish to sell, it is easier to sell (for example) two 150 point contracts than one 300 point contract...almost surely you will get more per point on the smaller ones.
Also, if you want you can sell one of the 150 point contracts down the road and still have the other one. With the large contract, it's all or nothing!
If you can handle the little bit of logistical issues, I'd go for the two smaller contracts.