Interested to hear from others on this one:
For me, the winter is my peak observing season. I live fairly far north, with astronomical dusk at 6:30pm, and astronomical dawn at 6:30am. 12 hours of glorious galaxy- and nebula-hunting darkness! What more could a person ask for (other than clear skies)?
The other side of the coin is that it's cold here. Often -20C or thereabouts. But you just gotta dress for battle. Do whatever it takes.
I can often get a session of several hours in a morning before work, being able to observe until 6:30am without any interference of sunrise. And likewise in the evening, I can easily get in a lengthy multi-hour session and comfortably get to bed before midnight. This means I'm not just hoping for a clear weather window on a weekend during a new moon, but basically every single evening and morning all throughout the week. There is bound to be at least a few hours of clear sky sometime during the week where I can get out and see something.
Do you love or hate observing in winter?
For example, in the past 5 years, I usually get zero observing days in from May-August. That is when I take astronomy hiatus. 1:00am-2:00am is a no-go zone for me no matter what time of year it is. I'm not hard-core enough. Also, the perpetual midnight twilight in summer doesn't provide much motivation to stay up all night when the sky isn't even going to fully reach true darkness.
And, the bugs.