Structure and multiple classified and business listing options

I have read the community comments regarding the following — and some of the comments are really old — and much of what I read is not very promising — :slight_frown: so I want to verify —

Now I have in each city — business listings, classifieds, and real estate listings, medical tourism

And I have want to have business, classifieds, real estate on the front site — and when they click on one of them – I guess I can create a page that has all the cities on it — then when they click on a city —

it takes them to that cities sub-site and the classifieds, real estate and business will have all three items on their menus — so they can switch back – so the directory plugin would serve both business and medical tourism — and classified would server classfieids and real estate —

would I be able to use the same plugin twice in the same theme — with different custom post types — or would it be better to make each a sub-site and connected through the menu???

Now — I also have different ad or business listing packages — including 1 free, and 6 paid packages —

This is not possible with the plugins because they only allow paid or free, and not both and certainly does not allow multiple packages —

someone suggested using the membership – and role route — but someone else commented that it would take alot of customization in php to make that work — so with the current state of plugins — can I do that with the membership plugin?

Thanks for your input ahead of time – let me know if I am describing this in enough detail