To help determine which option is best, organizations should consider where SQL is being used in their environment. This will help organizations determine the size of the potential migration, along with how business-critical or sensitive the information stored in these databases is.
First, organizations should ask if any instances are business critical. If a significant amount of business-critical information is stored in these databases, the best decision is usually to upgrade to SQL 2017. SQL 2017 has the benefit of being located on-premises or in the cloud, and as a result it will cause less of a disruption for business processes and workflows. This way, hiccups in upgrading your SQL solution will be minimized.
Another situation to consider is regulatory requirements. Using Azure SQL can occasionally cause problems with software compliance, depending heavily on specific license agreements. This is because some license agreements forbid deployment in cloud environments. Alternatively, keeping SQL 2008 could cause a range of compliance challenges, meaning its generally a wise decision to not maintain a SQL 2008 instance following end of support. As a result, it would be wise to ensure that whichever option an organization settles on is compatible with compliance agreements.
Last, consider if there is any sensitive data in your SQL 2008 database. If there is sensitive data, then organizations must ensure that the migration away from SQL 2008 is accomplished on time. Otherwise, an organization could be at serious risk of catastrophic data breaches. To ensure that SQL is constantly up-to-date, consider Azure SQL which automatically updates to ensure a high standard of security in a cloud environment. On the other hand, if your customers are skeptical regarding the security of the cloud, an on-premise solution should be considered.