I'm 53, and in my younger days I may have opted for a Raptor myself, but my buying brand new every ~9 years my last new truck (before the 3.0) was a March 2010 before the Raptor was released. Back then at age 44 I had thought about waiting for the Raptor to come out, but my son just turned 16 and I handed him down my 2002 Tacoma 4x4 so that I could buy a 2010 F150 King Ranch. My experience with my 2010 KR with a short bed told me my next truck needed a long bed, and that along with my age scratched the Raptor off the list.
On my answer above to #2 about DEF, please see my posts in the "Def" thread that I made since that post above.
As far as concerns about cold weather starts, I left mine outside all night at -14F and it started up instantly as if it were parked in my +32F garage all night. I don't have the record, however, someone else has posted a successful outdoor start outside all night at -32F in Wisconsin when the Polar Vortex went through.
I know wreedsvt is planning on deleting his truck when he turns over 10,000 miles. I may delete mine sooner then later as well, as there is no emissions testing requirements in Minnesota. I did talk to the aftermarket guy at my Ford dealer about deleting, and he said keep all your removed parts, because he knows of a guy that traded in a deleted RAM 2500 to them that took an $8K hit on his trade in value for the cost to the dealer to purchase and put back in the emissions parts.
- you're not overthinking this, funny thing is that you and I are similar in this. I joined this forum April 2018 and bought my truck last week November, and I researched and researched and researched and test drove for a couple months until my woman told me not to come home that day unless I brought home a new truck, and oh by the way it has to have those massaging seats she said--no problem there as I wanted the King Ranch anyway. Her parents live ~5 hours away from us, and dontchaknow that she is running that massaging seat continuously the whole drive (reactivates with a button on the side of the seat after it times out every 20 minutes--I still have to reconfigure that setting in FORScan to up the timeout on her passenger seat to 60 minutes). Also, if you don't know about FORScan there is some more for you to learn about--it empowers you to make your F150 Power Stroke even better!
There is only so much research and test driving one can do before it is time to pull the trigger. Then, through being a member of this forum you can learn even more about your truck and share your experiences and learnings with others and learn from them as well.
One more thing, you are also coming from a 2010 to a 2018/2019. The features, especially safety wise and cameras everywhere are incredible. Test driving is one thing, owning is another! Once I drove 200-300 miles in my new truck "Turbo" my old truck "Wilbur" was fading fast "in the rear view mirror". I have no regrets of trading in my 2010 for this 2018, and know that in any situation I am getting 4-5 mpgs more than before and with better towing capabilities. Another surprise is that my insurance on the truck with the same coverages only went up ~$25/month, which I expected it to be much more.