The steel will not last as long as brass and may not give you any warning as to when it will fail. Steel (or aluminum) work hardens much quicker than brass and one reason it is not used for cases as much as brass. Steel also does not "spring back" as much as brass and is why it does not extract nearly as nicely. If I was reloading any steel I would surely just neck size and use very light loads.

I've seen a video of it and it can be done. But it really looks like a headache. Depending on how much free time you have, it may be worth it to you. I think most people would rather spend the extra money on brass. But you're right, they should be reloadable many more times then brass, lasting a good bit longer.