Two extremes for example.....My Dillon is set up for 223 ammo. I can load 100 rounds of blasting ammo in about 20 minutes. On the other hand, loading precision ammo for one of my bolt guns might take me hours if I am annealing as well.
Difficult to answer as there are many variables. A lot depends on the equipment you buy and the accuracy you seek to achieve.. (I just saw someone else posted before I did, guessing it is going to read similarly).
However - you asked for a time metric, so that's what I will provide. With some middle priced equipment and an eye for consistency, I hand loaded 50 rounds yesterday from annealing (my first step) to completed rounds. It took four hours.
Yesterday was not he norm - I typically have several batches in different stages. This speeds up things from a larger perspective.
It can help your brass last longer by keeping the necks from splitting, but most of the time, your primer pockets will open up before the necks split. Annealing is more for consistency in your neck tension, and therefore contributes to accuracy.
Using a Dillon 650 that's setup and tuned (I use separate toolheads which makes it faster and easier too) I no shit generate one round per pull of the lever. That's it, that simple. Occasionally I throw random loads and put them on the digital to make sure nothing has changed (the powder check works really well when tuned but won't show smaller variations). So a few hundred per hour if all is squared away.
Note I prep on the same press and that's a whole different operation but still speeds things up (expansion, sizing and trimming). I have another toolhead with just a decapping die that I use prior to tumbling in a concrete mixer with metal pins (best way for large quantities, US works great for smaller amounts). If you count in dirty brass to loaded ammo I guess 100 per hour is probably a good estimate.
I used to load more accurate loads on the single stage but now I only use it for pulling bullets, priming and swaging .50, etc., and I use the Dillon as usual but use the digital scale and dispenser.
Still, I'd start with a single stage because 1. you'll always have use for one no matter what 2. it may not be for you and this is a cheaper way to find out 3. it's slower and there are things you need to learn, muscle memory or by wrote or however you want to put it, but you need to develop a system that works for you and stick to it. My biggest screwup early on were light loads. I depended on a powder dispenser and randomly checked loads on a beam scale that came with it. But my lack of experience meant I wasn't comfortable with the dispenser and didn't realize how it worked with different powders. End result is several 9mm loads only had 1-2gr. when they should have had 5 or so (IIRC, forget the powder) and that translated in to bullets stuck in the barrel BUT with enough energy to cycle the action. We were farting around on the range one day and I let one of the other SDM instructors use my M9 and that ammo. Luckily he caught the light recoil and handed it back to me before firing a second time. It did this with another pistol, a Glock, and I knew it was the ammo. Years later I tore down the ammo and found ten out of five hundred were faulty, but it only takes one to fuck up your day.
Don't worry about how fast just yet, there are solutions for that. Worry about learning the fundamentals (best done with a single stage) and go from there. Most of the stuff you'll want will be individual tools anyway and you'll always have a use for the initial gear you get. The RCBS kit isn't a bad way to go, it's what I got.
As for annealing, again, I'd wait. If like me you wind up with tens of thousands of pieces of brass, the last thing you want is to add another step and it may be better to just use the brass a few time and then sell it. Let someone else anneal it. With some brass, like Lapua for instance, you will need an expander to open the case up (or else neck tension will be ridiculously tight, again, common with Lapua brass in .308-ish calibers).
Regarding Dillon presses, I really liked the 1050 but the 650 is a MUCH better deal, especially if you plan on using it for multiple calibers. For .50BMG, which takes FOREVER to load and is a pain in the ass, the Dillon press is a must IMO. Especially if you have lots of brass.
and a lot depends on how anal you are. I'm about 80%, when it comes to reloading for precision. Prepping brass is the most time consuming part, but the most variable, timewise, due to anality. Some brass prep steps need only be done once, others 'periodically', and others, every reload cycle.
Above all, CONSISTENCY is the key to tighter groups. Eliminate as many sources of variability as you can.
Below is a partial list of operations I could think of off the top of my head....
One time tasks-
Weighing/sorting virgin brass
deburring primer holes
Truing primer pockets
Initial length trim
Every reload cycle-
Clean & inspect
Measure & trim length (if needed)
Deburr and bevel case mouth
Guys, if I missed anything, let me know.
As for equipment, I'm a cheap bastard, and I like the one at a time loading process.
I use a single stage press- yes, it is the slowest possible way, but I like to think I get more consistency- BUT, I have no data to support that. YMMV
I 'batch & process' most steps- this is for prefired brass
Clean & inspect brass
Size and inspect
Clean again (to get the lube off)
Measure & trim and inspect, if needed
Deburr & bevel (if needed)
Hand prime and inspect
Store in box case mouth up until ready to load
Set up dies, run dummies to verify measurements (COAL)
I use a loading tray, and a short drop tube. Inspect each as they are placed in the tray
All loads trickled to weight, and dropped
Once a tray (or more) are complete, then seat projectiles.
Inspect, measure, and burn incense to the Rifle Gods, that they may smile on your efforts.
You'll notice the word 'inspect' a lot. If it's in your hand, it adds no real time to look at it; it won't hurt, and may help.