Winter stargazing in the US midwest is hit or miss (mostly misses)

Here is how my typical winter session goes, so far:

1) AM: check Clear Sky Chart. clear skies this evening!
2) PM: on the way home, Brr, it's cold.
3) after arriving: take the scope out, look at Jupiter with my son, go back inside to have dinner.
4) Afterwards, either of two things may happen:
     a. go back outside. clouds!? what!? or;
     b. ooh, clear skies. Start observing and wondering why the seeing is so bad. Turns out that my eyes are watering so much from the cold dry air. After 30 minutes, boots freeze to iced driveway and start to lose feeling in fingertips.
5) head back inside and thaw by the radiators.
6) browse astronomy forums.