Lots of pertinent questions! And then DeathBeforeDismount's comments, lol, although he does actually indirectly touch on a relevant point.
The amount of reloading I will be doing is not large - probably around 50, maybe up to 100 rounds a month. I know that I won't get to the point of net money savings for quite some time (although I will be saving between $1.20 and $1.80 per reloaded round); unfortunately, I have to drive at least an hour to get precision ammo. Following up on that, I have a flexible/irregular schedule and work from home about 50% of the time (IT consultant), so downtime is something I generally have plenty of. Plus, I'm a diagnosed insomniac. As @91Eunoz was saying, getting the right ammo has been problematic, so being able to produce it myself would be nice.
Regarding accuracy: I am able to hit 0.5MoA 5-shot groups, but not every time. I know that I don't need handloads yet, but they can't hurt.
I already have brass brushes (among other cleaning supplies), metal tweezers, and hand and power tools.
I looked at the AGS annealer that was recommended, but am leaning towards the Burstfire Gen 2 Annealer & Prep Center due to it's greater automation and the powered tool stations.
@fedupflyer Thank you for the tip regarding air movement/dust covers. I was already aware, but appreciate it nonetheless! I have found the Ohaus Scout available used for $200-250, so I'm thinking of grabbing that. My plan is to use a scoop or cheap dispenser (like the $25 Lee Precision Powder dispenser) to get close to my desired charge, then finish it manually with a trickler.