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I am not working, and it was summer when I had LO so keep that in mind with my advice. I got one sleep bra that still had a thick band on the bottom for some support. It was stretchy and although I get up to DD, it's a D and still fits comfortably. I also got one that is wireless with slight padding to wear out of the house. I didn't have too many leaking issues, but when I did, this worked well to hide that if I was out without a pad. I also got a pretty underwire one, mostly because I needed to wear a dress to a wedding and didn't want to look frumpy/needed more support. I have worn it maybe 3 times. Any other time, I just wore nursing tank tops. I found that these with a cardigan (open or otherwise) were the easiest. Even though I was DD, I still felt supported in them. The bras I have were all from target, and the tanks were from walmart. When I am at home (which is often) I usually just go braless. Keep in mind that you'll have to wash these OFTEN, so I bought ones that were cheap that I knew I could just throw in the washing machine and not worry about wrecking. And, I was a 40D at the end of my pregnancy, and now at 4mos PP I am a 36DD. Just to give you a little perspective.

1. How many nursing bras do you think is ideal? I had 3 and that was sufficient for me but I didn't have leaking issues.
2. Does it make sense to have one that is more structured (i.e. with wire, shaping, etc) for the day and going to work, and one that is soft to sleep or lounge around in? That depends on you. I went back to work at 8 weeks pp and nursed and pumped for 7 additional months and I didn't feel it was necessary to have a nursing bra with more structure than the ones I'm going to recommend in your 4th question. I did get a few new blouses for work that were a little higher in the neckline because my nursing bras were higher than my pre-pregnancy bras though.
3. How many cup sizes did you go up from third trimester to after your baby was born? About 2 but my breasts didn't change at all during pregnancy so only after my milk came in. I waited to buy bras until 6 days pp.
4. Any recs? Elomi or Anita are great brands for a high quality nursing bra.

@JessLC: to be honest, none of my bras are the exact right size now. Both wireless ones are 40D- one bought ay 40 weeks, the other at 2 weeks pp. The wired one is a 38DD, but I have lost weight since I bought it, so the band size isn't quite right. Bought at probably 5 weeks pp. Not sure that answers your question, but there you have it

1. How many nursing bras do you think is ideal? I have 4 bras and 2 tanks and that is plenty for now while I am at home.
2. Does it make sense to have one that is more structured (i.e. with wire, shaping, etc) I wear a lot of layers so I am just sticking with what I have for now.
3. How many cup sizes did you go up from third trimester to after your baby was born? I was wearing only yoga bras from 20 weeks on...I was a size small, like 34B, but now I have to wear at least a medium and am probably a C cup.
4. Any recs? Love Target nursing bras and the Bravado tank at Target! By far my fav.

Any advice would be much appreciated!

@turtledoves
i bought 2 before baby and went and got 2 more and 2 tanks the week after i had him...and score they were on sale!

1. How many nursing bras do you think is ideal?
I have probably 10 nursing tanks. But we only do laundry once a week. So I needed more to keep up.

2. Does it make sense to have one that is more structured (i.e. with wire, shaping, etc) for the day and going to work, and one that is soft to sleep or lounge around in?
I just wore my nursing tanks to work. I didn't like my structured bras because they weren't as comfortable.

3. How many cup sizes did you go up from third trimester to after your baby was born? I'd ideally like to buy one that I can maybe wear now (33 weeks and I'm growing out of my current band size) and then be able to fit into after baby gets here.
With the tanks it didn't matter much. From my more structured I went up one size. So from a large to an xlarge. Mostly because I wanted to have less tightness.

4. Any recs?
I have had good luck with Target tanks but I have heard that isn't universal.

1. How many nursing bras do you think is ideal?
Let me preface this by saying I HATE doing laundry, so you probably don't need as many as I have! I have 3 nursing underwire/well supported bras and 3 comfy nursing sleep bras. In addition I use 2 sport bras I found at JC Penney with a zipper down the front for night. I also use 3 other non-nursing bras that have underwire and just pull the cups down - I don't care if they get messed up by doing this since they were inexpensive.

2. Does it make sense to have one that is more structured (i.e. with wire, shaping, etc) for the day and going to work, and one that is soft to sleep or lounge around in?
Yes - I would recommend buying a few of both. For night, I wear a nursing tank from Target and a sleep bra as I need the extra support. The sleep bras are typically very thin and after you nurse, your nipples will definitely show through so you'll want a more padded, structured bra if you plan on leaving the house.

3. How many cup sizes did you go up from third trimester to after your baby was born? I'd ideally like to buy one that I can maybe wear now (33 weeks and I'm growing out of my current band size) and then be able to fit into after baby gets here.
I went from a D/DD depending on the brand to an E (I bought all my nursing bras at Motherhood Maternity). However, I probably should have gone with an F as one of my boobs tends to spill out when I'm full (hate how it's just one!) I refuse to buy any new bras until I'm done nursing, though, so I just deal with it.

4. Any recs?
I would recommend buying your sleep bras now, as those are pretty flexible in sizing. I would recommend also buying a nursing tank with a shelf bra built in. This way you could wear the sleep bra and nursing tank on the way home from the hospital and then also if you need to go out and about the first couple weeks. I would say wait until 2 weeks postpartum to buy your underwire bras, as you may grow a lot once your milk comes in. I wish I waited - I bought my bras at 38 weeks pregnant and had to go back and exchange them a week postpartum.

1. 1 have 3 real ones and one stretchy one
2. Eh... the stretchy one is not that great--no support, might as well have gotten a much cheaper yoga bra
**I sleep on a towel folded in quarters because I tend to leak a lot and I sleep on my tummy (probably part of why I leak). Also I hate sleeping in a bra.
3. ZERO! Gained 6 inches in first 20 weeks (dd to g and 1 band size). Gained 1 inch when my milk came in but it went away. almost 4 months pp and down 3 inches again (but the ones I bought still look fine for some reason). BUT some people have a very different experience. I only bought one nursing bra before LO arrived.
4. My most comfy AND pretty is from le mystere. My hot milk one is ok but the clasp is nice. I actually cut off the full sling (uncomfy!). My other one is a non-nursing bra from a fancy lingerie store--they added clasps (no sling at all) to that bra that I bought when I was 8 months pregnant. I LOVE that bra.