I'm mostly planning to ease into reloading for my hunting rifles (not as interested in my handguns, at least not right now)... so a couple questions:
1. What manual would you recommend?
2. Would you recommend starting with a kit or just buying equipment separately and piecing one together?
There a lot of good manuals around, and several manufacturers of projectiles and propellant have on-line resources.
You'll get a lot of opinions about what brand of gear and what particular bits of equipment you need, much of which frankly reflects posters' own usage and often prejudices or brand loyalties. Before deciding what to get it would be a good plan to consider why you wan to reload, because that will make a difference to what you'll need and indeed whether it is worth reloading at all.
For example, if you only use a few rounds a year, in a reasonably available calibre, and your rifle shoots it well enough, there might not be much value in reloading. You might also get by with something really quite basic, if a little slow, to knock up enough ammo for the year if you don't use much. I personally started out with a Lee Loader, about 40 years ago, which is a very basic and admittedly rather slow way of doing it, but this is quite capable of making accurate and reliable ammo. It is also very portable, and will pay for itself if you factory rounds are expensive. It is not perhaps ideal if you want to knock up more than a box or two at a time though.
If you want to make ammo a bit faster, and/or have a bit more control over variables such as charge weight, seating depth etc, to allow a bit more "tweaking", there are various press kits. The Lee Anniversary kit is pretty good value IMHO, and I've been very happy with a predecessor for decades. Others may prefer different brands, but I've found that Lee gear is well able to produce accurate and reliable ammunition - several of my hunting rifles average well under 1 moa with ammunition made on a Lee O-frame press with Lee dies and propellant thrown in a Lee Perfect thrower.
There is dearer gear too of course, and for some applications like benchrest competition, or pumping out high volumes, you might want to buy some more specialised stuff, but for use in hunting rifles these really offer no benefit IMHO. No doubt that reflects my own prejudices too of course ;-)