I am currently breastfeeding my second daughter...did not with the first. I had a terrible time in the beginning, because she could not latch properly, but after a month or two of using a nipple shield, she (and I) got the hang of it and were able to feed directly from the breast.
I will just be honest with you...because of improper latch in the beginning, my nipples became cracked, and would not heal (I tried everything) and I went through infection after infection, spanning five months. After four courses of different antibiotics, the infection FINALLY cleared.
So, the first two months were okay, the third through seventh were EXCRUCIATING. I don't know why I didn't give up...in fact, I did start to give up, cried and cried, bought a can of formula (soy, as she is allergic to milk) and began allowing a supplemental bottle once a day. It was like that was all the break my body needed, and I healed!
So now, at eight months, breastfeeding is WONDERFUL. It doesn't hurt at all, is so convenient (always has been convenient), it is FREE, and what a wonderful bonding experience to share with your baby.
Most people don't experience what I did. It might hurt a little at first while your nipples toughen up, but as long as your baby latches properly and you are infection free, it will be smooth sailing.
My advice for a great start...nurse every two hours, at least, for as long as your baby wants to nurse that often...a month, two months, three months, whatever. That will build up your supply.
To begin pumping with a young infant, pump to empty the breasts after a feeding...I like to pump directly into Medela bottles, pop on a cap, and put them in the fridge. I line them up from front to back...every time I put a new one in, it goes at the back of the line, and when I take one out, I take the one from the beginning of the line...that insures good rotation. I have stored milk up to six days and used it with no problem.
Set out a bottle several hours before you will want it, so it can fully come up to room temperature. While you can't do that with formula, breast milk is safe at room temperature up to eight hours. I have left my milk out as long as six hours, myself, and used it with no problems with spit up, etc.
Personally, I do not like milk storage bags, and I do not freeze milk because regardless of what anyone says, it somewhat changes the consistency. If you feed a bottle, pump to make up for it, and put that in the fridge. That's how a keep a stock in the fridge (for outings, emergencies, whatever) and if I know it's coming up on the 6th day, I will just feed it to her, and pump to put a new one in.
Once you get into the rhythm and flow of it, it will all make sense and just seem natural. I think everyone has to work out their own system. I pray for the best for you, and wish you well...just give it a chance!