I do load development whenever it's convenient. That's usually in spring or early summer when the temps are cooler. I like to avoid heating up the barrel too much, so fire 3 to 5 rounds, then let the temp drop down until it's cool to the touch.
I first do a pressure test to find how high I can go with powder. When I find max, which is the max velocity that the cartridge is supposed to get, I load that powder charge, then go down from there in 1% increments for a 5 or 6 steps. I load 10 of each and shoot at distance. Usually over 500 yards and on a calm day in the early morning.
I look at the pattern of how the shots impact on paper, mostly looking at vertical, but horizontal is important too. Most times it's pretty clear where the load is most happy. Sometimes it's near the top and sometimes it's near the bottom.
I take the best powder charge and do a seating depth test at .003" apart for 5 or 6 increments loading 10 of each and also shoot them at distance. Usually there will be 2 or 3 adjacent cbto lengths that shoot better. I pick the longest one and call it done.
The velocity that the finished load is getting is the velocity I try to keep the load at regardless of ambient temperature. To do that I tweaking the powder charge up or down depending on expected temperature trends. Less powder in summer and more powder in fall and winter. I figure if the velocity stays the same, the load stays in tune and never goes over pressure.