The first question is the current generation and how many hops the move covers.
The line runs from Agresso Milestone 4 and Milestone 5 to Unit4 Business World 7.4 through 7.8, then Unit4 cloud 26.x. A single-version step inside 7.x and a jump from a milestone release into the cloud are different propositions. The measure is how much configuration was built against behaviour the target release changes quietly.
For each hop, ask which HR and payroll process areas change behaviour and which change only appearance. The first group needs proving from first principles, the second a regression pass. A plan that does not separate them over-tests and misses the date, or under-tests and finds defects after cutover.