Hi Chris,
Everything you have described in your list CAN be done in ArcGIS Pro using the SDK via an AddIn.
The question is whether you will target ArcGIS Pro 2.x or 3.x. I can't tell you what to use but I do recommend that you target ArcGIS Pro 3. The documentation is current for that version and finding older documentation could be problematic.
I recommend that you read through the sdk wiki on GitHub at Home · Esri/arcgis-pro-sdk Wiki (github.com). It is well written and has lots and lots of details. They also have a set of samples you can clone from GitHub. I made extensive use of the samples to understand how things work.
Creating tools (for layout), buttons for the ribbon, etc., is very easy in ArcGIS Pro. I think you will enjoy using the SDK.
Since you mention Windows Forms, I do need to point out that AGP3 targets .NET6. AGP2 targets .NET Framework 4.8. Don't let that discourage you though. It doesn't sound like your code is super extensive so getting it .NET 6 read should not be all that difficult (I could be wrong - just making an assumption here - and comparing to my own very extensive product line that took months to move to net6). Again, don't get discouraged.
Microsoft has really good documentation on the migration from .NET Framework to .NET 5+. Check this out - Migrate a Windows Forms app to .NET 5 - Windows Forms .NET | Microsoft Learn. Although it says .NET 5, it does apply to .NET 5+.
If your code base is 100% C# then the migration should go very, very smoothly. If you have 3rd party user controls, you'll need to upgrade to net6 compatible versions. At this point, all the major vendors have net6 compatible controls.
Good luck and have some fun.
Kris