My parents, sisters, and any aunts/uncles nearby that I support are all on windows 10 with android phones.
My results.
1. Time spend supporting family 1/10th compared to before. Android phones just work for us, update often and cost less so the occasional "OMG I dropped my phone and its broken" issues pretty much went away.
2. Android phones are all running the latest OS, give or take a minor update (usually stick with google or samsung flagship or mid-range models). Updating doesn't brick or blow away app settings or cause issues for users.
3. Never had this issue, but most of my family doesn't use facebook on their phones.
4. I have yet to have an apple product last more than 2-3 years. My last iphone lasted 1.5 years before it started randomly crashing/glitching. My current android is 2 years in without any issues.
5. Skype/Duo works great for my family. There is a subset of the family that uses facetime, they don't talk to the rest of us as often anymore.
I use apple products for work. I tend to get a HW replacement for laptops every 18-24 months due to HW failures, I'm on my 4th laptop in 6 years all due to HW issues.
Sometimes its got to be just luck. we have almost exact opposite experiences