Your post may be long, but an interesting read as I can relate to your question having been down the same road with 2 cars.
The Escort may be worthless, but it's not about value, it's about special meaning to you , if you have the space hang on to the car for as long as your emotions tell you, becauce if you don't , you will be thinking back a few years from now " why did I let that Escort leave me "
You mentioned cold winters, that brings me to the question, how is the body and frame ?
As for present thoughts, you are many months away having to make a final decision.