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Posts do not go on top of decking. Posts are structural and need to have bearing on to a sill or other structural member that is usually directly over and bearing on a foundation or "pier" foundation. Also, you need to account for attachment specifications and shear requirements and any other local code stipulations.
If you don't understand any of the above paragraph, then you should probably not do this yourself. This kind of work usually requires a building permit. It is possible that you could get someone to come and draw you plans that you could build yourself that would satisfy the local building dept.
For the siding, I would call 2 or 3 companies to get their estimates. Then, you could measure your house and windows, etc. and go to Home Depot for them to quote you on materials for doing it yourself.
I don't mean to sound harsh regarding the roof and posts. It is just one of those things where "if you have to ask" you probably shouldn't be doing it. Also, it really isn't possible for anyone to give you specific advise on exactly how to do it online. You can only tell this stuff on-site.
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