Welcome to the Q&A Forum

It sounds like you just want to pass on some of the link love your older stuff has which does not require cloaking.

Look into a 301 redirect.

I would utilize WordPress for the domain and use Pages as they override categories so you could loose one directory level of depth.

This would allow you to have a structure one level higher than what your current longtail landers are.

You would create your categories based on your longtail keywords and then create a page that is named the same as your category.  This way you could have your static lander for the top level of the long tail such as "red monkeys" and then use posts to target "red monkeys with tails" and "red monkeys without tails" and "red monkeys with randfish".

You could go all page rank sculpty with your navigation but then SEO Theory would hunt you down and shake you.

My 2 cents.

So:

domain.com = domain.com/main-section-1/ Set to Homepage

domain.com/main-section-2/ Category Overwritten by Page

domain.com/LTK1/SS1 Category Overwritten by Page > Post

domain.com/LTK2/ Category Overwritten by Page

Are you trying to create a new website for each individual Coach that is listed on your friends website that lists a bunch of different Coaches?

If so then why wouldn't you?

Are you trying to create a second tier of websites to promote the top "Coaching" website for purposes of link manipulation?

If so then make it look like you are creating a website for an individual coach or websites that discuss coaches in a general location.  When I say make it look like this assumes you know what can get you in trouble with a search engine.  If you have to ask what that is you should not attempt this.