I will be loading single stage
Trimming actually does matter. UNIFORMITY matters. Length (to a point) does not. You are going to be processing your brass batch wise, right? By the box, 50,100, or by doing them all, and then moving on to the next step in the loading process.
Sizing is very straightforward, and carbide .44 mag dies don't even require any lube.
Case mouth expanding & flaring (and they are two different things, done at the same time) is the first place where uniform case length pays a dividend.
(if you already know this, please disregard)
The lower part of the expander stem performs the same function as the expander ball in a bottle neck rifle die. The case neck is resized in the sizer die, leaving it too small to accept a bullet. The mouth is returned to the correct size by the expander ball when you pull the case out of the rifle die. Straight wall cases use 2 dies to do this.
Now, you need to flare the case mouth just enough to squarely start a bullet. The "step" up portion of the expander plug does this. You will have to find the adjustment for what is just the right amount of flare by trial and error.
Don't flare enough, can't start the bullets /shave lead. Flare too much, the brass is worked too much, and can fail very early (a couple of loading, maybe)
This is where uniformity comes in. If you use a short case, to adjust your dies, a long case will get too much flare, or crimp. Use a long case and the short one doesn't get enough flare, or crimp.
Pistol cases usually don't grow like rifle brass, but the do sometimes grow some. Check for length, once in a while. You will probably only very rarely need to trim because of excessive length.
Trim once, for uniformity, (trim to the length of the shortest case), adjust your flare and crimp on that, and you will be good to go, and not have the issues of one case getting too much, and another not enough.
An alternate method that also works is to separate you brass into batches by length, and adjust dies as needed for each different length batch. Its a bit more labor intensive overall, but it can be done.
Crimp for revolvers is kind of like Goldilocks. There is too hard, too soft, and just right. And which is which varies a bit, with the specific gun and load you are using.
Another tip, one that hopefully you are already doing with rifle loads, is to set the charged cases in the loading block (and with a good light) check the powder levels for uniformity. This is very important with pistol rounds, because many of the powders used can be double (or sometimes even triple) charged without overflowing the case. VERY important when using the fast pistol powders! A double charge of Bullseye (or anything similar) can destroy your gun. (Even a Ruger!!) A double charge of a slow powder (2400 etc) won't all fit in the case, so that's an immediate STOP sign.
Fast powder won't warn you like that, so you HAVE to do a visual inspection to be certain, BEFORE you seat the bullets.
I have other tips, collected over four and a half decades of reloading (3 of them pre-internet). If you have a question, ask. Please. If you don't understand the answer, ask again. We've got a broad expanse of experience here at TFL, and the odds are good that whatever you need to know, someone here knows it, and someone here can explain it is a way you can understand.
They might not, however, be the same person.