Have you looked into renting an electric pump from your hospital/health unit/pharmacy? I was not aware you could get these from the hospitals, and they worked really well for me when I had to pump a 5 days supply for my DS.
Our pediatrician has a different view on the whole cows milk before a year issue... he feels that as long as the child is getting a varied diet, eating solids well, and is eating a variety of meaty DAILY, then he is okay with beginning to wean onto milk at 8 months. I know this is not what the current recommendations are, and I've questioned him, but he's the head of pediatrics at the University Hospital... so I figure he must have a good basis for this recommendation. I'm not saying to go and feed your child milk, but if you are confident they are getting a sufficient intake of iron, he may be okay?! I'd do some reading before you make a decision either way, or maybe someone else on this forum has some info??
Also, have you tried straw cups or the soft sippi cups? My DS prefers a straw cup, we thought he would not take a sippi cup either. Other than that, that's all I can think of to suggest!!