In your case the problem I see is that you are using a lot products from Apple. In my case is just Keynote, otherwise I'm using just the OS itself, and I even h

In your case the problem I see is that you are using a lot products from Apple. In my case is just Keynote, otherwise I'm using just the OS itself, and I even have an Android phone, so the switch could be simpler. Unfortunately I think you'll require to do researches for each single software in order to potentially migrate to something else. The good thing is that for almost everything there is some indie solution that is great, but the bad thing is that it's not as simple as just sitting and letting Apple provide good integrated solutions. For iMessage however I would go towards Whatsapp, it's going to happen anyway world-wide IMHO, it's just North America that is using Apple messaging mostly. I totally agree it is significantly simpler to switch to Windows + VM or Windows in dual boot than bare Linux.