The first question is the one most programme plans assume rather than answer: which generation are you actually on, and how many hops does this move cover.
The line runs from Agresso Milestone 4 and Milestone 5, through Unit4 Business World 7.4 to 7.8, and on into the Unit4 cloud 26.x generation. A single-version step inside the 7.x range is a different proposition from a move that crosses from a milestone release into the cloud generation, and the difference is not measured in downtime. It is measured in how much of your configuration was built against behaviour the target release changes quietly.
Ask the question in this form: for each hop, which HR and payroll process areas change behaviour, and which change only appearance. Anything in the first group needs proving from first principles. Anything in the second needs a regression pass and no more. A plan that does not separate the two will either over-test and miss the date, or under-test and find the defects after cut-over. Cloud-readiness posture is one of the six domains a structured diagnostic assesses, precisely because it is the one most often assumed rather than measured.