I definitely wasn't a natural either but we managed to make it work. I almost don't believe people that say they enjoyed it, found it easy, etc. I hated every minute of breastfeeding but did it for my daughter because I knew it was best for her. I never understood the "fun for me" part of it.
I have no experience with mastitis and feel for you on that.
Here's how I made it work (with my equally negative attitude).
-I took a BF class at my hospital and saved the materials. The class hooked me up with a lactation consultant before my daughter was even born and provided me with materials that I could re-visit when things got tough.
-I prepared myself for the fact that it would be hard and reminded myself of that every time I got frustrated. I would tell myself that I knew it was going to be hard and that whatever I was going through was only part of the battle.
-I nursed often! I nursed every 2 hours (from start of a session so in reality there was only 1:30 between sessions) until my milk came in to ensure a good supply then went to every 3 hours for the first month. This was the advice of my lactation consultant to best avoid supply problems and it worked. I never made too much, but always made just enough so I can see how I would not have made enough had I not nursed as often out the gate.
-I set small goals.. first three months, then six, then a year, then until I could get my daughter to drink cows milk haha. The last three (12-15) months were her choice, not mine.
Good luck!!!!! Although I didn't enjoy a minute of it (and refuse to believe I'm in the minority) I take pride in each month.