System looks great!
Q1: There isn't a whole lot of difference between most coolers if they are decent quality. The PCCG Red Devil cards aren't the special edition, either. I personally got the cheapest 5700 XT (XFX RAW II) and it is almost the exact same in terms of temperature and performance.
Q2: Don't really have enough knowledge in that area to help with that.
Q3: Honestly Windows 10 is stable enough now that I recommend upgrading. A new PC would be a great time to do so.
Q4: I personally find Samsung SSDs to be the most reliable. The data on my PC is more valuable to me than upgrading a GPU, but it's totally up to you -- can't really go wrong!
Side note: I've never used PC Part Picker, but it may be cheaper if you get all the parts from the same site (shipping). I use PCCG and they also offer a building service where they'll build the system for you.