Possible Clues:

• Scaffolding erector
• Scaffolder
• Oil platform worker
• Fiddler in a put-up job
• Sailor, at times
• Long, pointed brush used by artists
• Outfitter who means to manipulate elections
• SQUARE-___ (KIND OF BOAT)
• One erecting scaffold to start going topless
• Worker on scaffolding being extremely careful, it's said