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Yeah I trust him, plus he seems to know what he's talking about/has had more work done on his house and apparently the roofers will give us a discount. I guess if I don't do it, first I'll probably know about any problem will be a leak, so it might be worthwhile.
His house is on the market, so it's a bit strange that he's looking to get it sorted now rather than later.
You on good terms and trust him? Would that mean the scaffolding he has to put up for his job means you now share the cost?
That said if yours actually does need doing it’s a good time to share the cost. Maybe get the roofers that are doing his to give you a show of what they think needs doing.