Each person is on their own, but I started with the Lee O press single stage, upgraded to the Lee Turret press and was frustrated to never end with their equipment. Got out of reloading for a few years for various reasons, time, and equipment costs. I eventually got back in it when I purchased a used RCBS Rockchucker, this used press was so much better to work with than the new Lee equipment. I would take others suggestions on buying something a little better to initially start out with so you have no equipment issues. Lee has the Classic Cast, which looks to be a lot better than the original Challenger one, the Pro 1000 might be ok, but have never used that one.
RCBS, Dillon and possibly the Hornady equipment.
It is like buying a $10 mountain bike at the pawn shop and trying to go ride some trails in the mountains, get better equipment or you'll regret it. The reloading presses and dies usually bring 50% and better on your money invested if you have to sell it because you didn't like reloading.