Your big problem is the roof, which can go from 5k to 10k, depending on how much plywood underneath the shingles has to be replaced.
The interior repair in that room due to previous leakage is likely to be:
Replace affected drywall, ceiling, possibly insulation, and paint. About $600.
The interior repair in that room due to previous leakage is likely to be:
Replace affected drywall, ceiling, possibly insulation, and paint. About $600.