Advice needed about starting a new site

I have what I think is a good idea for a new web-based business, but I'm stuck, I don't know how to make what I want happen.

At launch I need a site and mobile apps that allow easy bookings and payment, secure communication between two parties, search sort and taxonomy, customs statistics and profiles. I guess the closest existing design would be that of a dating service. There are other non-essential functions I would like to add later. I want speed and simplicity for the end user.

I've tried to cobble something together using wordpress, but it isn't working out. I could probably eventually do it by hacking something together using paid plugins, but the whole think would be a mish-mash of plugins from different developers, have a lot of potential for plugin incompatibility, and would probably cost thousands of dollars for the plugins I would need, which is out of my price range. I've had a few quotes from freelancers and local businesses that range from $4000-$15,000 and I don't even know if I'll be happy with the finished product.

Right now I know basic html and CSS and can put a simple page together. What amount of time am I realistically looking at to learn the skills required to be able to complete this project without paying for outside help? What languages do I need to focus on? If 400-600 hours I will learn the skills myself, that puts my rate at $7.50-$10 per hour, I have nothing else to do right now anyway and have a casual interest in web development. If significantly more than $600 I would be better off getting a day job and paying someone else to build for me.

Right now I want to get started developing the business but lack of skills and lacking of money is holding me back either way :|