The first thing to decide is the type of press you're interested in. There are three main types - single stage, turret or progressive. The reloading process entails the use of several dies that must each be applied to each round, affecting the basic reloading tasks of pressing out the spent primer, resizing the case, seating the bullet, and optionally crimping it in place. The means for applying each to each round is where the press types fundamentally differ.
- Single stage - a simple mechanical ram press that holds one die at a time. Dies must be changed and cases run through press multiple times to apply each die to each round.
- Turret press - press that holds multiple dies, but only uses one per lever stroke. The dies rotate to align with the round, applying each to each round via multiple lever stokes per round.
- Progressive press - press holds multiple dies, uses all of them on each lever stroke. Multiple rounds are in process at all times, so a finished round is produced with every lever stroke.
Many reloaders start with a single stage press, and as long as you don't intend to produce hundreds of rounds per week it's a great learning tool. Single stage presses are also have the highest degree of inherent precision, so if your accuracy-obsessed this may be an advantage worth pursuing. Single stage presses are also the least expensive inherently, increasing their appeal to those needing to purchase everything as opposed to those upgrading an existing unit.
I started with the popular Lee Classic Turret press, as I load a few hundred rounds of 9mm per week at minimum. Once the round count increases into the hundreds per week the speed advantages inherent in a turret press become attractive, especially as they aren't that much more money than single stage units. Progressive presses cost considerably more and are more complicated, making their tremendous speed something most beginners do without until they learn the basics of reloading with simpler units.
Kits may or may not save you money, as they often come with a rudimentary scale or other items you'd really like to upgrade right out of the gate. With Lee products the kits are pretty aggressively priced, though, so you can't get hurt very badly. You might consider a Lee Challenger single stage, but there are many good choices. I am familiar with the Lee products, but RCBS makes higher quality single stage presses you might consider if you feel you'll stay with the single stage for the long term as apposed to using it as a stepping stone to a turret or progressive setup. Due to their simplicity single stage presses aren't that expensive to manufacture, so while even a ~$70 Lee Challenger is a pretty nice press more expensive ones aren't that much more.
Once you've decided on a press type people can give you better advice on the exact product selection. You'll need to consider dies, priming tools, case prep tools and powder handling in addition to the press itself, but you can work out those details more easily once you've defined your press type and goals for its use.