Domain Names: Best structure for multiple keyword-specific domains

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Let's say you own:

and also derivatives:

What's the best way to connect all of these in order to not hurt yourself in rankings, traffic, SEO and, ultimately, sales?

I'm assuming one would forward the derivative domains to specific pages on the primary domain. In other words:

Might forward to:

Is it better to 301 in-server or to use the registrar to forward the domains?

I can see a 301 in-server could make for easier management and perhaps even give you better control.

Any difference?

Another alternative is to actually have one page sites for all derivative domains. There would be some derivative-related blurb on there and either automatically forward to the correct page on the main site or provide a button to do so.

Maybe there's another approach I haven't thought about.

Finally, I guess, at some level, there's the question of whether or not this is even worth it. You could buy dozens of domains containing minor and major deviations from your primary keywords. Is this ever worth it? Do you actively do this? If so, do you place an upper limit on how many derivative or related domains you purchase and vector to the main site?

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