New mom, I have questions!!!

Kayla • Married & we had our perfect baby boy on 03/21/2015, Pierce Huntlee. He was 7lbs 10oz, & 19.5 in 💙
Hi, I'm Kayla. I'm 27 weeks with my first and I plan to breastfeed, and bottle feed with pumped bottles. Just looking for some insight on this. I have so many questions because no one in my family really breastfed. 
How many of you had babies be able to transition back and forth from breast to bottle? Any advise? 
Also, working moms.. How did it go pumping at work, and did your supply stay up? 
Any advise is greatly appreciated. I'm determined although a lot of people in my family are not supportive and think it's "awkward." ?