I want to match the recoil of factory ammo and I also want to make sure it was going to make it out of the barrel. I was loading some at 3.3gr of 231 and people posted up concerns of it not being enough. Most suggested 4.0 to 4.3, so that is where I put them.
I'd probably check out what the factory ammo's velocity was, look at powders that delivered that velocity at the middle of their range, and then (if I had a further choice) select a powder with a burn rate in the middle of that bunch.
WW-231 (also sold as HP-38) isn't the fastest-burning powder out there, but it does produce light recoil in my experience. That said, you'll likely be able to produce a load you're pleased with, as it's capable of delivering decent velocities.
What is the purpose of loading up starting at the bottom? Assuming the loader does his job correctly. I checked, double checked, and quadruple checked my loads to make sure it was correct. Feel free to be blunt, you won't hurt my feelings. I'm here to learn.
Usually, it's erring on the side of caution, and a desire to use as little powder, recoil, velocity, and gun wear as possible to achieve the desired results. Let's face it, if you were working up a light target load with a soft wadcutter, why bother going to the midrange?
Now, you don't
always have to start at the bottom of a powder's range, once you get a little experience.
For instance, in my previous example of loading some funtimes .44 Mag with 185-grain LRNs and Titegroup, the Hodgdon data goes from 5.3 to 6.6 grains. The maximum pressure is 16,500 PSI, and the maximum velocity is 1,082 fps.
If my goal is a punchy, fun-to-shoot load, why bother with the 5.3?
Now, I'm familiar with the cartridge, powder, bullet and gun involved. Titegroup is stable all the way up to .44 Mag's maximum pressure. The max listed pressure of 16,500 PSI is around half of the cartridge's spec.
And the velocity they stopped at with a cast bullet is 1,082 fps. They pushed it over 1,500 fps with jacketed data for the same powder.
Hence, I can reasonably conclude that they stopped at 6.6 grains and 1,082 FPS because they reached the limit of the bullet. The upper limit for lead is around 1,200 fps anyway, without a gas-check. That tells me that I've got a lot of headroom over the printed maximum.
So I'd probably start at around 6.6 grains. I might subtract a couple tenths of a grain to account for a little fluctuation in the powder measure's throws. Depending on the results, I might even go a little up from there--if the load didn't lead up the barrel, recoil too heavily, bang too loud, or perform inconsistently (recoil too heavily and bang too loud, but only
sometimes, which would scare me more than if it just did it consistently

). After all, I know more or less what a cartridge in that range should feel and sound like.
I wouldn't recommend that as a starting practice, or even a general one. Start off slow, take it easy, and enjoy the process. It's more rewarding that way when you end up with something you really like. Most of my favorite loads took some figuring out, but that's probably why they're my favorites.
That said, as you gain experience in reloading, and spend time studying the performance of different cartridges and components, the amount of figuring-out you have to do decreases.