If you have to buy brass, buy all the same brand at one time and you won't have to trim it. Most roll crimp seating dies will handle a .010" variation with no problem. I have all my .357 mag brass sort to two different lengths, all the different brands fall into these two different length groups with no problem.
If you use taper crimp as other members said, you don't have to trim at all. Since you stated you don't like heavy loads, a taper crimp may be the way to go.
I don't own one, I use a roll crimp die because I'm to cheap to buy a taper crimp die.
This whole crimp thing is not a quagmire and you don't need to be concerned over it. With loading for midrange loads you just don't need to have a roll crimp.
I would recommend you buy Starline brass if you have to buy brass. It will last you a long time. The last 300 Starline brass .357 mag cases I bought from Starline were all with in .006" of each other.
No case trimmer needed for that. Their new brass is worth the little extra price you have to pay for it.
Welcome to "wheel guns". It may take several years, but you'll finally get accustomed to not chasing your brass !!
I don't think it will take that long, but from chasing 9mms, that is funny, and very true.
For powders anything in the midrange burn rates work well but some don't meter well out of a powder measure. So be watch full for those. It your weighing on a beam scale and trickling then it doesn't matter.
My favorites are BE86, Power Pistol, and Universal with BE86 being my most favorite.
I have found 7.3grs of BE86 to be my most accurate load with plated Extreme SWC 158gr bullets with .357mag cases.
Power Pistol ended up being 7.2gr and 7.8gr loads with the same bullet.
You will enjoy the journey so let us know how you make out.