As someone who switched from Iphone to Android, I will say there are some growing pains when transitioning.(Like getting rid of your iMessage account stuff so other iphones recognize you can no longer accept iMessage) Biggest issue I see from your list is the Apple Watch compatibility. They make great android watches, it just sucks since you already invested in the Apple Watch. I am rocking the S8+ right now, had a Note5 before that, and LG G Series before that. I am very happy with the Samsung products. Being that your a techie guy, I see where you will enjoy the customization abilities of the android. The one plus of the new phone plans, no contract is locking you in for 2 years so worse case scenario, you pay off the phone and switch back, sell the phone to recoup any losses.