A pitched roof can be installed over an existing flat roof and you just add some roofing trusses onto the roof or frame the roof trusses onto the flat roof yourself.
You just need to attach the pitched roof trusses to the existing flat roof and then apply your roofing materials to the roof.
Having a contractor do the job can cost around $3,000.00 to $6,000.00 but if you do it yourself you can usually add the pitched roof onto the flat roof for around $1,000.00 or a bit more depending on the cost of materials.