Another good idea would be to hire an architect to draw up the addition. They don't charge a whole lot for concept drawings and they can make it look like part of the house rather than an attachment to the house if you know what I mean.You are going to have to deal with the main level windows being in the way of your new roofline.
If your house looks like the pic than you should have no issues attaching to it. Pouring a footing and a slab and then building should be relatively pain free. Concrete is pretty expensive, at least a third of your total.
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