Disclaimer: The opinions in this article are purely mine, and may or may not apply to your scenario. Please take this as purely another viewpoint in your analysis. No warranties made.

In the previous article I examined the use case for moving to cloud in the first place. Assuming you have decided to move to cloud, the cross roads we now stand is at whether it needs to be Project for Web or Project Online.

Just to level set, Project Online benefits from decades of development for Project Server and has all the features of that have been developed over time. This includes Complex Scheduling Engine, Stage Gate Workflows, Timesheets, baselines, Critical Paths etc., These are not available in Project for Web yet, (without the custom development work in Power Apps and/or Power Automate).

Now at the same time, Project for Web has features that focus on Simple Scheduling like building schedules, creating dependencies. It also has additional features that Project Online does not have currently, like Co-Authoring, No Check In-Check Out of projects, Easier assignment of resources, integration with MS Teams etc.,

So, in summary, these are a lot of ‘it depends’ answers. The risk here is that Microsoft officially states that Project Online will be legacy at some point, but does not clarify how soon it will happen.

The list below are the questions you need to ask your self which could help arrive with an answer.

1. Do you need to move to Cloud? What advantage does the cloud give you to moving to on-premises version of next version?
2. If you do need to move to cloud, how rigorous is your project management team’s usage of the tool? Will they miss features like Scheduling Engine, Stage Gate Workflows, Timesheets, baselines, Critical Paths etc ? Will they miss the use of MS Project as a scheduling tool?
3. Is your organization ready to adopt the newer version, and spend some additional funds to bridge the gap of functionality? Or is your organization ready to adopt Project Online right now and then later adopt Project for Web when ready?

In summary, while the answer depends and differs for each organization, in my opinion, if the organization has adopted cloud/O-365 already, AND moving your project management solution to cloud makes sense, it seems appropriate to move to project online now, and let Project for Web catch up in feature parity., At that time, it might be easier to do a controlled roll over. Again, just a reminder that this is my personal opinion, and not a universally applicable advice.