I started with the Lee Pro 1000 as my first jump into reloading. In addition to the press and consumables, I bought a RCBS 505 scale used from ebay for about $20. The only other thing close to being a "must have" is the sorter/funnel that goes on top of the case feeder tubes. For $15, its well worth it in time savings. Also, Richard Lee's "Modern Reloading" book has a lot of load data, in addition to some helpful tips on setting up his presses and is also worth while.
The Pro 1000 has a bit of a learning curve, but its not insurmountable. Its big weakness is the primer feed system, which likes to sometimes flip primers and will sometimes fail to feed if the primer chute isn't kept full. To remedy this, I load rounds in two steps. First, I deprime/resize and prime - doing this with the powder measure removed from the press. Next, I remove the depriming pin and run the primed cases through again, adding powder and bullets. This way, there is now powder jumping out of cases to jam up the primer feeder, and if there is a badly primed case, I can pull it out of the batch without having to deal with pulling a bullet or dealing with spilled powder. I still manage to load a few hundred rounds per hour ( 500 rounds in 2 hours without pushing it ) splitting the loading process into two steps.
The Pro 1000 works well and makes quality ammo. With its low start-up price, I recouped my initial investment in the press and scale after about 800 rounds. The fact that the Lee press costs 1/3 to 1/4 of a comperable blue, green, or "other" red press makes the ocasional tinkering worthwhile for me. If I had to spend $700-800 on a reloading set-up, I wouldn't be able to afford to reload and I'd shoot a LOT less. If I were to do it over, I'd stick with Lee, but I'd consider spending the extra $100 for the loadmaster. After loading for about 2 years with the Pro 1000, the ability to load rifle cases, and the extra die station would be nice, but not necessary, for me.