Tires Tyres Llantas

Should I throw some new rubber on this thing?  Change the oil? (just changed it in Oct)  The rubber is now getting down there since this photo was taken.  I used to nut & bolt this baby - check everything.  It's turned into this "jump on and go" bike.  That's asking for trouble.  Do I risk it?  Hell, run it to the Shuffle and Dice and update it before Sturgis.  Just ride the SOB !  The Black Bike has never let me down.  Ever.