DS is only 3 days old and I'm already frustrated with nipple shields!

DS initially had feeding problems because he swallowed a lot of fluid and blood on the way out. He spit up quite a bit for the first 24-36 hours and wouldn't eat because his stomach still had all that stuff in it. The first LC I saw said I had flat nipples, gave me a nipple shield, and pretty much just left. It didn't help much. The next day, another LC consultant came by and actually showed us how to use it properly. DS did a great job nursing with it. Things were looking up. Now that he was understanding latch a bit better, we were able to get him to nurse without the nipple shield a few times.

Now that we're home, things aren't going the way I would like. I know he can nurse without the shield, but he's much better with the shield. The problem is, I can't put it on by myself, If I try to nurse without it first, he gets so frustrated that he's screaming by the time DH comes over to help me get the shield on. He nurses well with it on, but when he pulls off I see milk left between the shield and my nipple (stuff that he sucked out but didn't swallow).

Did you use a nipple shield? Any tips on getting it on? How long did you need it? The second LC I saw said some women use it for their whole BFing time.