In my opinion the hardest thing in linux is leave to use propietary or exclusive software for windows, the first think you must do is leave to use propietary software in windows, and when you can live without windows exclusive programs, switch to linux. You can start for ubuntu or other linux friendly distribution, doesn't care, afther the migration you can try other for curiosity without risk
In my firs time with linux I install ubuntu (maybe 12.04, I dont't remember, it was gnome 2) in the only PC in my parents home, I delete windows, and we was using it 2 years without knowing what is a terminal and everything went fine, the problems appeard when I was discover the terminal hahahaha