Doing your own reloading is really not a big deal, it does take some research, and there is tons of proven information available out there to work off of. I have not reloaded and shells in quite a few years, but I did at one time have a Lee Loadall I think it was called. It's a nice entry level setup, and for a couple hundred rounds here and there it should work out fine for you. First thing you will learn is what brand cases work better, and which ones don't.
The winchester cases worked best for me, Remington was not too bad, nor were the Peters cases. I was never a big fan of federals or other cases, they just never seemed to recrimp quite as good as the Winchesters. Something else you may want to invest in is a gram scale, just to verify powder and shot charges, especially if your going to be trying various powder brands
Have fun and enjoy, but do the research, and don't go experimenting just for kicks, bad things can happen then.