How to list nodes in a view as checkboxes?
You'll have to test that particular combination yourself, but there are modules that seem the best fit to try first. 

To be able to select individual views results and perform actions on them you need Views Bulk Operations (VBO). You don't need to look further than that module for this part. 

The tricky part is the PDF. Views PDF and Printer, email and PDF versions might have helped in D7 but they don't seem to be ready in D8. 

In D8 Entity Print seems to be the rightful heir so try that one. Also I don't know how far you can get without custom code. You will probably need to use Rules to create the action that would be executed with VBO.