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Whilst many roll off roof observatories tend to be built by owners, rather than contractors; that's not to say it isn't possible since all it is essentially is a structure (like a big shed) all the way up to the wall top plate with a separate sliding roof.
If you already have a design in mind or plans then a competent builder would be a good 1st place to start, simply advise them of your various special requirements such as the concrete footing/foundation for the pier and any motorization you may need on the roof, which is not dissimilar to sliding gate automation with a motor/gear rack drive. The builder may also be able to help with any design or regulatory approvals and/or recommend a designer/architect if required depending on the structure's size and position.
Best
JA
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