DTW has a good airport hotel on site, the Westin. The airport must confuse new hires beacuse they use unpublished frequencies and odd ball change over points, but Kennedy often just tells you to monitor ground so they have more time to scream at Air France for making wrong turns on to active runways. The sooner you learn to just roll with it the happier you will be. The only big, efficient, perfectly logical, operation on the planet is Atlanta. You will also observe any airport US Air operates from is a complete ATC disaster.

New York has improved a bunch with the new facilities and will only get better.

I'd say it is a toss up. Both have really good Captains and good operations. Some of my favorites are in both bases. You will have fun.