Breastfeeding & flat nipples/large breasts & necessary items

J.
Sorry so long! But my questions are... 
Any tips/tricks or personal stories for a very large breasted woman with FLAT nipples. Maybe slightly inverted, but they don't completely disappear inside, more like when you mimic bf, then it's just flat areola, no real nipple protusion. I've read quite a bit online, but still looking for personal stories of what worked etc. 
Also... Necessary/unnecessary items... I hate to spend a lot of $$ on pump & supplies if I won't be successful. I figure Amazon Prime will get me whatever I need within a few days. Anything I should definitely have on hand? For example... Boppy/bf pillow? Necessary? I sleep alone with like 10 pillows. Can't I just use my pillows when bf?Should I buy a manual inexpensive pump to start? 
My background...
baby #1, I was well-informed, took bf classes, had all the equip & worked with consultants prior (and after) delivery in order to bf. I had a complicated delivery, 9lb 5oz baby with fractured clavicle, my body went into shock, my milk never came in & baby never could latch. I ended up pumping for 6-8 weeks to supplement formula. It was exhausting and mentally draining. Baby #2, induced early with easy birth. My boob was bigger than the baby's head. I still tried, but was very emotional and decided to give up within a week. Then I experienced my milk coming in and always wondered if I could have bf her. 
Fast forward about 13 years... Baby #3 coming in December. Emotionally I feel more capable of handling life with a newborn. But... I am doing this alone, no boyfriend or hubby, just my 2 teenagers in the house. So there is no 2nd hand for help or support. I would like to make a good attempt to breastfeed. But I'll also be going back to work within 4 weeks (3 days/week) and won't really be able to pump much or at all during work. Plus after 6 weeks, if needed, then I will get on an anti depressant, such as Paxil. 
I appreciate any suggestions or personal stories. TIA! 
 
I pumped for 6-8 weeks to supplement. It was exhausting, I was very depressed & anxious. I had taken bf courses, had all the equipment etc. But So baby #2, I tried, didn't feel successful and didn't feel mentally stable enough for the pressure, so I made decision not to bf (then for 1st time I experienced milk coming in about a week after birth). Now I'm 12 years older lol. I'm emotionally in a better spot, although I'm doing this alone, there is no boyfriend or hubby to help with baby. My boobs are big. Right now (22 w 1d) I'm busting out of my normal DD size. And my nipples are flat. So even when I mess with them, once I mimic bf all that's left is a flat areola with hardly any nipple protusion. I desperately want to try again.