Sorry a late reply but maybe it can still help.
Have you already decided what to do?
I like your site ideas and i think self knowledge is something we can all use a lot more of!
I always end up doing things the complicated way, not by design but it usually turns out that way
So when i read your post i noticed a few things:
It might not seem much but keeping 3 sites updated with new content takes time, especially if you don’t really love writing (and good curating is a lot of work)
It also means sending traffic to 3 different sites
Are you doing this on your own or do you have help?
If it was me i would skip the blog and create 1 big brand with the DDL being part of that brand but on a separate site
(that is if you don’t want to sell it separately in the future)
A bit like the food channel (or any other network) promoting different shows they created under 1 big brand, with 1 product logo and the main brand logo or a mix of both
You can then do that for other products like the dating one too (or have the option to do so)
I would keep the emails separate so each site has their own follow up but you could add a comment to the signature that says something like DDL is part of SKC so people know about it.
Then add those emails as blog posts to the sites (as Jim suggests in the training)
This way you are repurposing the emails + you still have a blog
It does seem to me like the SKC will cover a lot of different topics.
How do you plan to give people the info they are looking for?
Though a personal quiz?
Specific email follow ups?
Do you keep it general?
(see me making things more complicated again)
That’s all I can think of for now hope it helped.
When you get this all sorted out and you have a plan it does become a lot easier