Hello @aeryk-pierson ,
Welcome to the wonderful world of Windows!
I would recommend starting with the Windows 10 (MD-100 exam). This exam focuses on deploying, managing and maintaining Windows 10. It reminds me of a more traditional approach to managing the client, locally installed, configuring settings, etc.
Then I would suggest the Managing Modern Desktops (MD-101 exam). This exam also deals with managing Windows 10 devices, but focuses on more modern management techniques. Things like using Windows Autopilot to deploy the OS, joining devices to Azure AD, using Intune to manage devices and apps.
With these to exams, you will have the skill set to manage Windows 10 in any environment, on-premises, hybrid, or cloud-only.
Also, once you pass both exams, you will receive the Microsoft 365 Certified: Modern Desktop Administrator Associate certification!!
The 70-697 and 70-698 exams have both been retired. They are worth watching, much of the information is still relevant, but I wouldn't spend too much time on them. Watch them when (if) you have spare time.
Then I would shift focus to Azure. Most organizations have moved at least some resources to the cloud. Depending on your experience, AZ-900 (Azure Fundamentals) or AZ-103 (Azure Administrator) might be a good place to start. AZ-900 if you are brand new to Azure, AZ-103 if you are familiar with Azure.
Microsoft is releasing updated exams for Azure, for example AZ-103 is being replaced with AZ-104. This isn't supposed to happen until early April 2020, but something to keep in mind as your studies progress.
Hope this helps!.
Let me know if you have any more questions, about exams or as you are studying!