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Mornin' Wab!
Being a die hard DIY'er I would definately do all you described above myself. Contracters these days are so busy making big bucks with new construction that all I could get to come to my house are incompetent rookies or thieves.
ONE STEP AT A TIME. Your project list is huge and I would spend several months getting it done at a comfortable pace. I would start organizing my thoughts with a CAD program like Floor Plan or similar to help me picture the end point.
Other thoughts - Plan your deck utilize standard lumber lengths to minimize waste. I'm returning several dead azaleas to HD today. Most plants even trees are guaranteed for 1 year. The deer ate them. I saved the receipts and tags off the limbs.
Plan and enjoy.
BUM
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In a panamax down by the river.
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