OK. Let me just break this down to you country simple because I can relate to a lot of your original post.
Based on this quote
"Getting a new car is more of a want than a need; I can afford it, and at this point in my life (approaching 60) I would like a more refined and up-to-date vehicle"
You should buy the Golf. The Focus is not the car for you. Forget all the other stuff about filters and commute and blah blah blah.
In my opinion, taking nothing away from Ford..I've owned them..I even had a Focus, and going from a Fit to Focus is a total lateral move. The ride, comfort, refinement, handling, styling, and just that solid thud of the German VW door closing...those are the things you want. You deserve. And will not find in a Ford or Mazda or any Japanese car. If you buy anything less than what you REALLY want, ie The Golf TDI, you will regret it.
I have a 2015 Golf TDI SEL. I traded in a Volvo XC 60 and then a Subaru Forester on my search. I test drove the BMW X1, X3, Audi A4, Q5, (I can afford them easily) and then the Passat, And Golf. Every day I'm driving my Golf I know I made the right decision and it is the right car and perfect mix of refinement, fun, and economy. PS I live in Worcester Massachusetts. Similar to Chicago as far as climate and as a matter of fact for the past two years we were the snowiest city in the Continental US. That said, I have had NO problem with starts or fuel filters ...or anything after 30k. And I drive short trips to my kids school and then long commutes to NJ and NY. And, my FWD Golf with awesome snow tires, is by far, the best handling car in the snow I've ever had. And I've had a lot of AWD SUVs.
Good luck and post a pic of you and your Golf when you get it.