If you have the time to do SEO yourself then you can learn online for free.
Benefits: you save your $1000
Risk: you get it wrong and don't rank, you make little or no money from your site
Even when you know SEO well it takes a lot of hard work to get a website to rank if there is already competition there. If you're learning then you can make mistakes and waste time.
So if you need to spend most of your time running your business (and it's a new business) then you should pay someone else to do it for you.
If you have a lot of time to learn, or if your business is already doing well and profit from your website would be a nice extra, then you can teach yourself.
One word of warning. Once you start learning SEO do not try it out on your site straight away. Unless you are lucky, a lot of what you will read is wrong. Make sure you understand what you're doing before you do it and PLAN your web strategy. Don't just do the first thing you read about.
If you want to pay to learn SEO then two of the best places are going to be SEOBook.com and SEOMoz.org. Costs about $200/month for each one, but they also have a lot of free information.
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