How the heck do I upload images to a post that doesn't wrap all the text around it?

This is what you keep ending up with:

This is what you want it to look like:

STEP 1

Upload your attachments like normal.

STEP 2

Click to edit image.

STEP 3

Set alignment to 'Baseline' & update.

STEP 4

If it still doesn't look quite right, try putting a line or 2 between your text and image.