Thanks for your responces, and I apologize I forgot to mention I am talking about my 1987 300TD (going to edit post now).

@cscmc1 - that is a super slick move, I never thought of that before! I would suppose as long as you don't get wax on the inside of the belt it won't slip. Interesting tip!

@1985300D - Pulley bearing was actually my first thought -- again I wanted second opinions though -- what's the worse that could happen, it ceases? Yes I plan to pop the hood after work today before I start it and video/take a look. It may be so loud though at first that I may have trouble finding where it is coming from.

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'87 300TD Estate (Panzer Wagon, Sold)
'95 E320 Estate (Sabertooth, Sold)
'94 E500 (Stark 1, For Sale)
'04 VW GTI (Rhino, Sold)
'12 VW GTI Autobahn (Shadow)