I posted something similar to this in the general forum, but I think it got deleted for being in the wrong forum.
Anyway, that was a long post so this one I'll boil down to the main points.
SEO can take a lot of time, so outsourcing is a logical step. It allows you to work on many pages in the time that it would take you to work on one.
When you outsource, do you like to buy packages (article submissions, social bookmarks, etc.) or do you like to hire VA's and teach them what you want them to do?
Or, do you hire someone already skilled in SEO and let him use his better judgement?
Also, you probably want to have an understanding of how much traffic a page will get for a given keyword so you can estimate how much it will make you. After all, you don't want to spend $1,000 to rank a page that will make you $50 a month (unless you have a very large budget).
Thanks for any sights you guys can give into the process of outsourcing SEO!