Possible Clues:

• Playwright has Romeo fencing?
• Glass ceiling in block
• A stumbling block with first barrel - there's no head on the porter
• Advocate getting shot of street obstacle
• Brexit negotiator swaps note with Republican fence
• Hurdle
• Fence? Cross-country runner needs new start
• Stockade maybe is more exposed blocking raid, oddly
• Black bird removing hard obstacle
• Playwright sitting on top of retaining wall