Some crowdsourcing please?

I'm pregnant and would like to try to breastfeed, provided that my body/baby cooperate with each other. I'm the first of my group of friends to have kids, and am a little lost and overwhelmed with all of the information out there.

This is what I look like when trying to figure out these things on my own. Any suggestions/advice you have would be great.

1. I've heard that breast pumps might be covered under insurance. Has anyone purchased on that way? Did you find that there were plenty to choose one, or did your insurance just cover a bare bones model?

2. Do you have a model of breast pump to recommend?

3. What were the biggest challenges you faced?

4. I know the laws specify that women are to be given flexible time in a private place to pump. I'm a teacher, though, and I have NO IDEA how this would work...like are they just expecting me to pump on my lunch? Even if you're not a teacher, do you have a similar job that can be...really really *not* flexible with that sort of thing? How did you make it work?

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5. If you had the option to do everything over again, would you breastfeed?

Here, have a cute picture in return for your help: