Monty81, welcome to the HDTimeline forum. While others will weigh in shortly, I guess I need some questions answered. 1) Depending on which cover you are talking about, the derby cover will not let you see very much, and being as you have a 2000 Sporty, I would remove the primary cover as one unit...then you can inspect EVERYTHING and be out only the additional $25-30 for the gasket. That way you can check the cam chain tensioner shoe, inspect for metal debris in the corners of that cover and surrounding area, and really inspect the back side of the clutch cable and how it passes thru for possible future problems best avoided now. 2) Do you have a tech manual, Torx and Hex Fastener tools, 3) Space set aside for tilting the primary cover and working on the bike from the side stand side?, 4) Do you have consumables and parts on hand that you EXPECT you will need, 5) Did you "reherse" the sequence you wanted to disassemble and inspect and leave yourself plenty of time for "multiple" trips to the dealer or indy for additional parts you may need once in there?
If the color of the fluid, or the smell is burnt, brown in color (should be pale honey color) you will know how how far you want to go. I always start the process on Friday evening, so I have two full days to get additional parts or take the time without rushing. I use my Sporty as my daily driver, so downtime is critical to me...the cost is secondary, time and preparation are a key to successful completion of the task.