I think that probably the most important thing to pass here is that with someone just starting out in the hobby, it's important to get the basic's down before going for volume. Therefore, I recommend a single stage reloading press, and I won't even bother to recommend a brand. It really doesn't matter which, but there are at least two schools of thought here.
1) Go cheap! (Lee - new) or second hand RCBS, and when the learning process is complete, trade it off and upgrade to a progressive.
2) Buy a Quality single stage (I prefer RCBS) and retain it for the more precision loads that aren't really possible with most of the progressives out there.
The key is that he (Snakeman) needs to learn the basics of how to make quality ammo. Learning how to adjust the dies, work up loads, fiddle with crimping methods, case resizing and care, etc, etc, etc. These are things which aren't learned overnight, and are better suited (in the learning process)for the single stage. Only after he understands what's happening with the single stage can he feel confident to make the progressive step (a little play on words there!) to cranking out a larger volume of shells with one of the more animated setups.
I have nothing against them, I just think that this sort of endeavor is best entered cautiously, and going whole hog with a newby and a multi-stage is the recipe for disaster.
Another thing that I don't think that I saw mentioned was reloading manuals. I cut my reloading teeth with a RCBS manual and a Lee loader, and now I can't seem get enough new literature related to loading. Not only is there a wealth of information on HOW, but there is plenty of WHY, WHO, and WHERE too. There is (collectively) hundreds of years of reloading experience packed into those books - and it shouldn't be ignored.