Do I need to purchase the business plan first and then add the domain, and then, do I need to do that over and over and over again for every single site that I would like to add on my account?
Go to My Site ->Plans and buy the plan. Then go to My Site ->Manage ->Domains ->Add Domain to register the domain.
Next go to My Sites ->Switch Site and select the next site, and repeat those steps. Do this for every site you want to update.
I would like to start with 2-3 websites and then build up to 15-20 websites that would have different topics that I love :D, maybe hire some writers in the future, or people could submit original content and get paid for it ( Can I do this ? Is that legal ? )
As long as you adhere to our user guidelines, you can create as many sites as you want, and post whatever you want on them. We have no problem with it if you pay other people to create content for you, as long as the content is original.
I cannot advise you whether or not this is legal as I’m not a lawyer, and don’t know the laws that might be governing this type of thing wherever you live, but I highly doubt that it won’t be.
One more thing, I would like to keep the domains on a different site, pay the bills for them there and just connect them on WordPress after I purchased the plan, can I do that for every single domain?
You can do this using our domain mapping option, yes.
https://en.support.wordpress.com/map-existing-domain/
It will still require a paid plan on each separate site you want to connect to its own domain.
