500 and under. But probably, if I'm being serious with myself, 400 and under. I like the idea and draw of being able to roll my own and tinker with the process.
Those distances, and not competing in an accuracy discipline (like benchrest) make things a whole lot more forgiving
A lot of people getting into reloading initially (myself included) want to make the BEST ammo possible at look at what the benchresters are doing. I bought "The Benchrest Shooting Primer" and studied the techniques when I only had factory Remington's. This was a waste of time; you can't see the difference in most of what they do unless you're doing ALL of it (rifles, rests, wind flags, etc) and it certainly doesn't make a difference in field shooting.
Powder dispensing:
I would consider a GOOD mechanical powder measure. I have a Harrell's Precision measure (I have their cheapest one, was ~ $200 at the time) that I use to load at the range or for some production loading situations. It is repeatable and FAST. I definitely prefer using it to something like a Chargemaster, and it is more portable and durable. You'll still need a scale, but a balance beam scale is fine for getting the measure calibrated. I should do a write up sometime on how I set mine up. You WILL have some variation in charge weight more than weighing every charge, and it won't show up on target. ***Warning - Extruded stick powders with large kernels are less smooth and less accurate with these measures***
If you do go with a cheapie electronic thrower, I'd get the Chargemaster and skip the rest. I HAD a Hornady, wouldn't recommend.
When I weigh charges, I use a FX120i/Autotrickler V2/Ingenuity Precision setup, which is fast and very accurate, but you have to piece everything together. It is the first place I'd splurge on fancy equipment for what I do.
Presses: almost all of them will work fine. The Rockchucker is solid, I like Hornady's bushing system, and the Forrester has excellent leverage. I do all my loading (except at the range) on a Hornady LNL AP progressive, but it would be hard to recommend to someone just getting started. The Zero looks like an amazing piece of equipment but I couldn't personally justify the cost, plus I really like my progressive and the workflows it allows.
Chronograph: very useful to confirm velocities especially when learning. Because velocity correlates so closely with pressure for a give cartridge/bullet/powder combination, it really helps let you know where you're at. For the distances you're shooting, you can get away with a LOT of velocity variation, so don't get hung up on SD or ES.
Budget choice: Magnetospeed sporter
Compact, more costly choice: Magnetospeed V3
Favorite: Labradar
Tumbler: I use a big dry media vibratory tumbler, and a media seperator to get the walnut media back out. I typically only tumble to get case sizing lube off, I could also wipe them with a towel but it's slower. I size brass dirty (unless it's actually muddy) and don't put much value on the shine. Wet tumbling with or without pins gets things really shiny but can introduce it's own issues, half the people I know who tried it switched back.
Annealing: getting started out, I'd opt to not mess with annealing. The primary advantage is brass life, the secondary is that if it is done well each load cycle behaves more consistently regarding sizing and neck tension. I do anneal some of my brass, and would love an AMP, but it is it's own rabbit hole and is optional IMO.
Case prep centers: I have one, almost never pull it out. I chamfer by hand when brass is brand new or when I trim, and I avoid trimming if at all possible. I don't brush necks and I never touch primer pockets. I would like a Giraud or Henderson trimmer, and would probably trim more often if I had one.
Measuring tools: I use the Hornady comparators to measure bullet seating depth and shoulder bump. There's way's around it but these are cheap and really useful to me. I have a basic (~ $50) dial caliper from Amazon I like, haven't embraced digital tools here.
Dies: I like the Redding micrometer seaters, but anything that will seat them straight will do. I also like bushing dies, as you can size the neck down just enough vs a standard die that will significantly oversize it, then bring it back up to the right size with an expander ball. You get straighter brass that has been worked less (less need to anneal) and grows less (less need to trim).
Brass: I like Lapua and Alpha, and I absolutely keep batches together. That said, it can all work, and work well, sometimes you have to run Hornady because that's what's available.
Got to get ready for the day, but that's a decent start. It can be a pretty deep rabbit hole.
Can you elaborate a bit on how things would change in yardage increments? Ie 500 and in, 500-700, 700+?
Mainly powder measuring, if I only shot 500 and in I'd probably throw everything always. The farther you go and the higher your expectations the more value there is in weighing to the kernel. I shoot a lot of 223 with thrown charges out of a Hornady powder measure that runs on my progressive, and around 700 you definitely notice the extra vertical dispersion start to show up, at 1000 it's very clear.