I do almost all of my observing from my house in Melbourne, a location where on some nights I struggle to see the fifth star in the Southern Cross :/
I almost exclusively observe with a 4" doublet where I spend most of my time viewing the moon or planets, so for me I don't do any planning.
Most of my observing sessions are quite short as well, mostly focus on imaging
Sometimes setup the little scope next to its slightly larger brother for something to do while running setup routines on the imaging run.
Around this time last year I was following the mind set that I really needed to upgrade my 12" to get more aperture. A year later I still plan on upgrading the 12" but going smaller (8"-10"), something that I am more likely to use! Even my longer observing sessions aren't long enough for the telescope to completely acclimatise considering some nasty temperature drops. My 12" is that telescope that sits in the garage (corner of a spare room) that only comes out when I do public outreach events. it is a telescope that I've setup for just myself literally a handful of times (4-6) in two and a half years. I have spent more time at the eye piece of my 4" in a month than with my 12" in 2.5 years. Comfort is also something to consider!