After the Panda update rolled out, the latent risk in such a strategy could (typically would) vastly exceed the direct cost of the content, as poor pages on one part of a site could drag down the ranking of other pages on the site which targeted different keywords. Some sites have seen their search traffic fall over 90% with their ad revenues falling even faster. Demand Media went from being worth a couple billion to tens of millions of Dollars. ArticlesBase.com sold on Flippa for $80,000, but was making over $500,000 PER MONTH in profit before getting hit by Panda. Many other Panda-torched sites like Suite101 have simply went offline.
The primary difference is that Long Tail Pro is a big time saver over MS. With Long Tail Pro you are able to enter in multiple seed keywords at once (rather than just 1 with MS). So, instead of entering in 1 seed keyword, waiting five minutes, then going back and entering in one more; you can enter 5 seed keywords (for example), hit generate and then see all the keyword ideas at once!
To answer your final question, yes but not really. You can definitely use AdWord keyword planner tool to get solid organic search volume estimates. However, don’t just stop there. Leverage other tools to find longer tail variations you can map against various stages of the buyer journey. I like to use SEMrush, Keyword Tool.io and Google autosuggest.
Understanding the balance of terms that might be a little more difficult due to competition, versus those terms that are a little more realistic, will help you maintain a similar balance that the mix of long-tail and head terms allows. Remember, the goal is to end up with a list of keywords that provide some quick wins but also helps you make progress toward bigger, more challenging SEO goals.
I just have the free version right now so I don't know all that the pro one can do. But even the free version has A LOT of tools you can use, I haven't even figured them all out yet. But one that I have used is their Content Optimizer. You can take a new or existing content piece of yours, and compare it to one of your competitor's pieces on a similar topic, and see where you might be lacking based on the keywords that are used in each piece.
The final sales price was based on a multiple of trailing 12 months net income (i.e. The average net income over the most recent 12 months).  I feel like I got a very good multiple.  I had talked to the brokers at FEinternational, Quiet Light Brokerage, and had viewed sale history of other similar companies, so I know the price I received was very competitive.
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