The last order the guy did for me consisted of around 700 rounds. About equally divided between 243, 280, and 308. The other calibers I'd be looking at are 7mmum, 270 and potentially 30-06.
For the 243, I can find cheap nosler's for it in factory loads at 95 grains, but the others I have a harder time find the appropriate loads. And the factory loads vary so much, the noslers for the 280 from winchester seem to explode on contact where as the federals provide a nice mushroom. Also, I have not been able to find fail-safes in most of the calibers I have for large game (elk).
As for price, I know that when I pay someone else for the reload work, I save about 40% off what I could be a standard factory load for. On top of that, the loads are usually top notch powders with consistent range and field performance.
The 700 rounds is about 3 years of shooting. My dad yells at me for shooting so much, but I like practicing and getting better. He's of the frame of mind I'll wear out the guns. My moto is use'em.

My younger brother does about 200 ever year or two, but he tends to have a larger variety of calibers.
I also look at reloading as a change of pace from the hectic computer work / games / electronics in my life. As I said, I've looked at doing this a number of times, but haven't done it for lack of space. 9 kids tends to leave no space available.
From what I know, since the 280 and 7mm are built on the 284 bullet, I'd only need the one die set to do that. The 308 and 243 would be another pair of die sets and then the 270 would be the 4th I added to the set. The 280/ 7mm Ultra are my primary guns and would cover my dad and my younger brother. Older brother chose 30-06 and my mom uses a 308.
I am looking at single stage and not progressive since I'd be looking at doing smaller runs then when I have them brought to a reloader. Fortunately the current reloader has provided the primer and powder information on the current runs, so I'd have a starting point to do the initial loads.
When I look at this more, I'll be in touch.