That isn't "sloppy", but as others have pointed out, it is just worn away. But, it does appear that the previous owner painted the waterline up higher than original, covering part of the molded in boot-top, it also appears that the hull was not properly prepared before doing so..... the paint covering part of the boot-top has flaked off due to the area not having been dewaxed and sanded enough. I have had small spots like that on my boat due to my habit of waxing the topsides before painting the bottom and any bare spots along the waterline naturally get wax on them. You might be able to carefully scrape the paint on the boot-top to remove, then compound it back to shiny and paint just up to the original line. Or, just tape off the raised line carefully and after cleaning the area that is flaking (use a recommended solvent), sand it and apply paint.