I've been thinking about this too. My interest has waned a little over the past year or so and I do put it down to the weather. Most of my imaging (or even straight observation) is done in the presence of our club members at either of our two dark sky sites - one darker than the other. Of course, the darker one is twice the disctance away....
The main problem is in lining up
organised sessions with the weather. There seem to be plenty of nights when I'm home that I look outside and think "wow - what a gorgeous evening - I hope it'll be OK on Saturday". If I had an observatory at home (which I'm resigned to now) I know I'd be able to just pop out for a quick fix while the weather was behaving and be happy. As Paul says, it's the repetitive setting up/aligning/clouding up/pulling down dissappointment cycle that is the killer. I can't remember a good night with my club mates where everything just went "right" - it must be months ago. Adding to the frustration is the ritual that starts with charging batteries the night before, piling everything into the car, organising dinner snacks and coffee, driving out there, setting up.... etc, etc - you know how it goes.
I've just convinced Jenny that a slab and permanent pier are required to save my sanity - to which she has agreed. At least I can trundle the G11 equatorial head outside and set up with verry little drifting required. This alone will save my bacon I reckon.
I have taken up another hobby (apart from the ubiquitous photography) which I was into decades ago - radio controlled flying. At least I can build and tinker on those nights the weather isn't playing ball - only to be faced with Saturday or Sunday winds and rain - "flying is off for the day"! Grrrr Another weather-dependant hobby!!!! You'd think I'd have learned by now......