Yes, Creative cloud allows you to work on both windows and MAC machines and also allows you to sync your files on the cloud so that you can work from wherever you want.
Yes, but use only fonts which are the very same on both OS. Best practice is to use only OTF fonts.
When you have linked files, avoid extended characters and spaces and Don't use / or : or \ in file names.
Package the project and transfer the whole project folder between the 2 computers.
And you must use the same version of InDesign on both platforms -- ID files are not backward compatible for earlier versions.