@s_mayhead, you are going to have a fantastic time with this project, but it _is_ big. So: my advice would be to take your time before planting anything. It may seem frustrating, but it will be the right course of action.
First, you'll need to fix the hard landscaping--walls, hard paving, extension, anything like that. This kind of work turns your garden into a quagmire and woodchips all your favourite plants. Having an empty space is the best way, therefore. You'll want to spend a good bit of time plotting where paths and seating areas should go, so if you can, try and measure up your plot and draw a plan which shows the fixed areas, with pencil marking for the current location of features that may want to go. John Brookes' books on design are helpful for this, and there is some good garden design software you can get as well.
Second, it sounds as if you already have a vision for the end result, which is great. Your first thought when it comes to planting should be about viewpoints. Are there any things across the boundaries or within the garden that you want to conceal? Think of where you may need to place hedges or trees to do that. At the same time, think about your need for particular spaces within the garden. Do you definitely want a compost heap, a shed, somewhere to sit near the house, veg beds, a chicken coop? Begin plotting where those will go, as well as the new pond. These sorts of things will all mark your fixed points, around which the design must work. Your paths will be the linking point between the house and other spaces in the garden. For example, if you want a washing line, you'll need a way to reach it easily. All these decisions also involve everyone else in the family.
Is there any area you'll need to enclose (e.g. pond, veg beds to keep dogs out)?
Making all these decisions first will then whittle down the space you have for ornamental planting. At that point you can follow your wishes for a cottage-garden style of planting and work out whether, for example, you want something with formal elements or more naturalistic-looking. Reading up will help. I find the books by people like Noel Kingsbury and Piet Oudolf very helpful, because they give information about the natural conditions of particular meadow-type plants which will help you work with rather than against your soil.
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@s_mayhead, you are going to have a fantastic time with this project, but it _is_ big. So: my advice would be to take your time before planting anything. It may seem frustrating, but it will be the right course of action.
First, you'll need to fix the hard landscaping--walls, hard paving, extension, anything like that. This kind of work turns your garden into a quagmire and woodchips all your favourite plants. Having an empty space is the best way, therefore. You'll want to spend a good bit of time plotting where paths and seating areas should go, so if you can, try and measure up your plot and draw a plan which shows the fixed areas, with pencil marking for the current location of features that may want to go. John Brookes' books on design are helpful for this, and there is some good garden design software you can get as well.
Second, it sounds as if you already have a vision for the end result, which is great. Your first thought when it comes to planting should be about viewpoints. Are there any things across the boundaries or within the garden that you want to conceal? Think of where you may need to place hedges or trees to do that. At the same time, think about your need for particular spaces within the garden. Do you definitely want a compost heap, a shed, somewhere to sit near the house, veg beds, a chicken coop? Begin plotting where those will go, as well as the new pond. These sorts of things will all mark your fixed points, around which the design must work. Your paths will be the linking point between the house and other spaces in the garden. For example, if you want a washing line, you'll need a way to reach it easily. All these decisions also involve everyone else in the family.
Is there any area you'll need to enclose (e.g. pond, veg beds to keep dogs out)?
Making all these decisions first will then whittle down the space you have for ornamental planting. At that point you can follow your wishes for a cottage-garden style of planting and work out whether, for example, you want something with formal elements or more naturalistic-looking. Reading up will help. I find the books by people like Noel Kingsbury and Piet Oudolf very helpful, because they give information about the natural conditions of particular meadow-type plants which will help you work with rather than against your soil.
Good luck, and do keep us posted!