Let a professional siding contractor and roofing contractor do the work. I can't tell you how many homes I have inspected that had sub-standard work on the siding and roofing that was done by the homeowner. You might very well be qualified to do the work, but if something goes wrong what then?
Most homeowners that get the money from their
insurance company tend to not do all of the work that is needed. They see the $$ and skip some the work. The big items get taken care of and the little items are skipped in an attempt to profit from the loss.
If you have hail damage to your roof and siding then you most likely have damage to all of the soft metals around the home. This would include vent, flashing, flue pipes, etc. Also you should look at the outside part of the HVAC system. Take a good look at the condenser coils, if they have hail dents and damage then that unit needs to be replaced as well. Take a look at the windows. Yep, if you have windows that have plastic parts, you will most likely find dings, dents and cracks on those parts.
Call the insurance company and let them send the adjuster and then hire a good contractor.