Get a good fat bike. You can spend some stupid money on one from a bike shop or do what I did. Purchased one for $500 and added another $300 or so in needed upgrades, not counting tires and $150 on accessories. Fat bikes are all about proper tire pressure for the conditions. And studded tires...
With brass being so soft compared to steel, a long time but I doubt I could even guess accurately. Probably the biggest mistake with these is running the drill at full speed and getting the cutter hot which will shorten the life a bit. They do sell replacement cutters (the bit) if needed.
World's Finest Trimmers. Have Have used the WFT-Original for several years and they work very well. And, the crank handled one are not fun if you have more than a few brass to process.
https://www.littlecrowgunworks.com/store1/Worlds-Finest-Trimmers-c31402021
Also a fan of the chargemaster. Several years of use and no complaints. My insert is a McDonalds straw and works perfectly. Never get an over-throw.
Couple more favorites just because.
Wore this one out and RCBS sent new parts to replace free of charge.