Must I upload a Featured Image for a blog post separately?

I'm creating a new blog for our site, which is on Squarespace v7.1. I've read https://support.squarespace.com/hc/en-us/articles/205812718-Adding-featured-images#toc-collection-item-featured-images but still have some questions about the Featured Image for a blog post and the Asset Library. I have loaded images into the Asset Library and organized them into a Blog Images folder. 

1. Does Squarespace automatically use the first image in my blog post for the Featured Image? Or, if I'm using the same image for both, do I need to add the image twice, once within the content of the post and again for the Featured Image in the post settings? The article referenced above states "By default, the first image that displays in the product editor becomes the featured image." but I'm assuming this is specific to product listings, not blog posts. 
2. Why can't I add a Featured Image using Select from Library? When I click to add a Featured Image I only have the option to upload an image. Am I missing something? 
3. I will not be the main blog content creator. If the other creators upload an image directly into a blog post, then upload the same image again as a Featured Image, will there now be 2 instances of the same image in the Asset Library? 
4. If I go back later and clean up the Asset Library and move blog images into my Blog Images folder will that break links to those images wherever they are referenced in the site?

Basically I'm trying to keep things organized and efficient. My process for now is I first upload the image as a Featured Image, then I go into the Asset Library and move the image into my Blog Images folder, then go back to my blog post and add the image into the content using Select from Library. This is ridiculous and tedious! 

TIA! 😄

Hi @RosettaHealth 

1 hour ago, RosettaHealth said:

1. Does Squarespace automatically use the first image in my blog post for the Featured Image?

No, it doesn't.

1 hour ago, RosettaHealth said:

     2. Why can't I add a Featured Image using Select from Library?

You can. 

When you're in Blog Post Settings, instead of clicking "Add Image", click on "Search for Images". This will bring up your library, and you can choose from there. See the screenshot below.

1 hour ago, RosettaHealth said:

      3. If the other creators upload an image directly into a blog post, then upload the same image again as a Featured Image, will there now be 2 instances of the same image in the Asset Library? 

Yes, but that is the same behaviour throughout the website, not just for blog posts. You can upload the same image to the Asset Library more than one time, and each time it treats it as a new asset.

1 hour ago, RosettaHealth said:

        4. If I go back later and clean up the Asset Library and move blog images into my Blog Images folder will that break links to those images wherever they are referenced in the site?

No, it won't. Folders in Asset Library are for you to organise your assets. The folders have no relation to the page location of an asset.

Hi @melody495!  Thank you so so much for your help!! 🙏 😃   You saved me a lot of frustration. Don't know how I missed the Search for Images in the Blog Post Settings. 🙄 

@RosettaHealth You are very welcome! Haha it's easily missed, it's not the most intuitive "click" function.