Hi @HarperS  I hope you are doing well. Based on my experience, please refer to the following points as the challenges I have encountered.

1. Lack of Clear Requirements

2. Resistance to Change

3. Over-Customization

4. Data Migration Challenges

5. Integration with Legacy Systems

6. User Training and Adoption

7.  Unrealistic Expectations

8. Complex Workflows

9. Governance and Role Management

10. Inadequate Testing.

If it is helpful, please mark it as helpful and accept the correct solution. In future it might be helpful to someone by refer to this solution.

Regards,

Wahid