I have bought "factory" reloaded ammo in the past with okay results. My weapons still function, and I still have my digits.. I prefer sealed surplus military ammo when possible though.
That said, I only reload for close friends, and immediate family, and that's it. Other people have asked me to reload ammo for them, and I politely decline their offer. I'll offer to help someone out, or answer questions to the best of my abilities if they want to start doing it for themselves, but that's about it when it comes to people outside immediate family or close friends. Typically for close friends we're reloading to troubleshoot an accuracy issue or some other issue with their weapon (like feeding) - not necessarily for any cost saving benefit, because in my experience it is generally more expensive to reload than to buy new ammo.
I seem to have a lot of the same equipment that Pomeroy has, mainly RCBS stuff, we have Lee factory crimp dies and a couple of redding dies as well. Most of my stuff is RCBS though. He said it though, buy quality once and don't look back. I like the idea of a progressive press, and it would save me a ton of time when reloading handgun ammo, but for me, I'd have to re-tool to go to one of those setups. It's easier for me to just get another single stage RCBS "rock chucker" and go about it that way.
I personally enjoy reloading ammo, the only tedious part for me is case trimming. That isn't my most favorite part, but you gotta take the good with the bad.. A friend of mine has a Dillon electric case trimmer that's mounted on the top of a single stage press that looks pretty nifty. I just don't usually have the $ for Dillon stuff..