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Help! How do you add a picture half way through a list on a blog page?

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I am writing a blog post that includes a list of points and I would like to put a photograph at the side of one of the points mid-way through my list.  I know that, in order to add a picture at the side of a writing block in a blog post, you have to first have an insert point and then click on the 'plus' button to add a new picture block.  Once you have chosen a picture, you can click and drag the picture to the side of the writing below the insert point.  

The thing that I am struggling with is how to get an insert point to appear mid-way through a numbered list. 

I've tried breaking up the text block so that the 'plus' button appears for a new block mid-way through my numbered list but it then creates a bit of a weird gap between two of the numbers in my list and also restarts the numbers from one.  I'm sure I can't be the only one who wants to put photographs beside a few items on a list but for some reason I have been unable to find the answer out online.  I don't think I'm terrible with technology but this really has me stumped and very frustrated!

Any advice would be much appreciated.

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