When I had a Type 6, I only had to carry $2M in general liability (pretty sure I could have gotten only $1M, but I chose additional coverage). Comparatively, I carry $1M now for general liability for my wife's bakery and our photography business. Total cost is $30-75/month. Insurance requirements are worse on commercial kitchens and trucking companies than on ammo manufacturers.
As a small shop making ammo with only one guy operating in his spare time, getting a couple of Autodrives on Dillon 1050/1100's work fine. The Camdex machines take a lot of time to payback, so a casual dude probably isn't quite where he needs to be to justify it. I helped two friends set up their ammo businesses in the last 7yrs, both are on robotic dillon presses. Setting up the vision systems to sort brass by cartridge, then by primer size and by primer type, plus the cleaning, swaging, trimming, and roll sizing gear were much higher priorities than the presses to do the actual loading.
Supply chain logistics are a pain in the butt. You're small, so you're basically just getting distributor pricing on most components (not exactly a rich retailer margin on wholesale prices), OR, you're buying massive bulk orders - I could never justify for myself to buy non-cannister powders in the volumes required. Getting enough of what you need, when you need it would be much harder today than it was when I was running mine (Clinton and Bush Jr era). Equally, balancing sales & marketing against production planning isn't something many folks are truly skilled to manage. I had a luxury of a relatively captive market when I was operating - I had a customer base of 3 gun competitors at multiple local ranges which bought thousands and thousands of rounds of 9mm, 45auto, x39, and 5.56 ammo - I paid back my first reloading machine within a month just working a few hours a night during the week to prep brass and full days on Sundays, and I was partnered with another gunsmith and trader hosting tables at gunshows every month for most of the year, putting that same ammo on tables with him sold like hotcakes too. Contracting range pickup brass from Ft. Riley also helped a lot too.
There's a bit to think about in beginning any business. Write up the plans, conduct the feasibility study, the answer will reveal itself quickly.