Firstly, congratulations!!!! It sounds like you're doing a fantastic job!
i had very similar attachment issues to what you've described. Everybody told me the attachment was 'perfect' but my nipples still looked like they had been butchered. I did also have inverted nipples which was a big contributing factor.
We used nipple shields exclusively from about 2 weeks, because it was the only way we were able to BF. For the first couple of months I was resigned to the fact that we would be using them for our entire breastfeeding relationship. But at around the 12 week mark I started attempting to get DS to attach directly to the boob. I started off doing one feed on each side a day and then gradually built up until after a few weeks we weren't using them anymore. We went on to breastfeed until 22 months without any issues.
As your bubs gets older you will find that his mouth gets bigger and his suck gets stronger, making it easier for him to attach correctly to the nipple. At this stage the most important thing to do is BF, shields or not shields. By using the shield you're going to be able build a breastfeeding relationship that isn't stressful and is enjoyable for you both. That is essential for long-term BF. But to answer your questions I would say 'no' to each and everyone of them.
As long as he has good wee's and poo's you don't need to worry about whether or not he's getting enough. Nipple shields these days are so thin that your aereola still gets a really good amount of stimulation so your milk drying up really isn't a concern. And based on my experience it is relatively easily to wean from them when you are both ready.
When we first started weaning from them I would give him the first side with the shield, then offer the second side without it. By this time he wasn't starving anymore so was willing to work a little harder at the attachment iykwim?
In terms of brands, I always found the Medella ones the best. They are hard to find and more expensive, but after trying pretty much every brand out there they were definatley worth it.
There have been quite a few threads like this, and from memory there are many women on here who have had long BF relationships with their little ones using nipple shields. Like I said, if nipple shields are going to allow you and your DS to establish a comfortable and enjoying BF relationship then there is nothing wrong with them.
Good Luck hun, and you are doing fantastically! Cracked nipples are the worst!Oh, the thing I found really good for healing my cracked nipples was giving them a saline bath after each feed. I'd just fill up a medicine glass and put my nipple into it to give it a good wash. It really helped them heal a lot faster than they were.
HTH


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Oh, the thing I found really good for healing my cracked nipples was giving them a saline bath after each feed. I'd just fill up a medicine glass and put my nipple into it to give it a good wash. It really helped them heal a lot faster than they were. 

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