Your on about the best tool for a first step, your computer.
A time saving approach is learn what has to be done, look at price and availability, then determine if its right for you.
Take your time with this and you will make better decisions.
If I could give you the number one pitfall most new people make, it would have to be looking only at which press. Actually sticking the powder in a case and seating a bullet is about the easiest and simplest part. One must first collect the components to be loaded, often have to clean brass then prep the brass, and all before you dump a single load of powder into a case.
Here's a decent site to get a rough idea what has to happen step by step:
RCBS Loading GuideThat of course does not include case cleaning but it should give you a first idea. Now depending on what you buy, you start combining those steps.
About the best place to learn what different "Types" of gear is Cabellas follow the links "Shooting Gear" and then to "Reloading". Spend some time learning what those differences are and the strengths and weaknesses of each one. Just keep in mind, a basic setup can do all the things a high priced advanced setup can and just like manufacturing what you are looking at when paying more is time savings. Don't just look at the kits or presses but spend sometime learning dies and the various tools to do the other jobs, what has an advantage and what doesn't.
Once you get to the point, you start seeing the Catch 22s like one should measure and trim used brass after resizing it which sort of defeats the purpose or defines the way a progressive die press should be used and understand that, then you're ready to start shopping in earnest. That's just an example, there are many but the main thing is you'll know when you start understanding what does what and why.
Kits are good way to get started but pay attention to what's in the kit. They often don't match up similar time saving techniques. When shopping and looking at kits its always best to compare individual component costs. Doing that now will help you later on once you start shopping in earnest. Its not uncommon at this stage to start researching different brands and reading posts on forums like this.
Now by this point you should know the different types of presses, why they are different, the different types of hand tools and secondary tools, why they are different, and different types of components (powder, bullets, brass, primers.)
Now its decision time on whether you think you have a good understanding or not. If there's still a doubt, buy a reloading manual first. They all go through the step by steps of what has to be done much better than that RCBS site I linked.
Some people just take a jump in buy a press or kit approach, but I actually (learned the hardway myself) consider that a more expensive approach in either cost or potential. Above all this is a lifestyle choice and unless (nothing wrong with this either) all you want to do is trash out one load on this or that caliber over and over again, no matter what you buy you will be buying more stuff down the road.
As far as aptitude goes, this isn't rocket science though God knows you can apply more engineering than you can imagine to it if you are so inclined. One should however have a basic mechanical aptitude and the more manufacturing experience one has the better. Loading involves a lot measurement and doing repetitive tasks so requires a good eye for detail. If one has an eye for detail and will constantly use that book as a reference on what to do and what not to do, starting out with a cook book mentality is not a bad thing. Like most things in life, the more you do the more you learn.
Once you have an idea of what you want, you can start shopping in earnest and you can even asked more detailed questions in forums like this, like whats the best this type of press or that type or what's the best scale, trimmer, etc. for this type press an these type volumes.
It all seems a bit daunting at first but really one can gain enough knowledge in just a few hours of reading to start making early decision paths and like many things in life you can change down the road once you get a better handle on it.
If one is truly into shooting, loading your own can be the most rewarding experience and decision one makes since they bought their first gun. Besides getting better ammunition for less, it will naturally make you a better shot and increase your entire shooting experience.
Tj