Hi there. Sounds like a nice project. I have built an extensive backend over the last 10 years for the yacht company that includes a major CMS tool for their website, controlling images and a tree structure. I also built my own directory sites that each had different features but together include the things you have mentioned: directory, classifieds, posting ads, some paid via paypal, different content displays per category, messaging system etc.
I could put this together within three days of starting and would ask for $200+freelancer fees.
I would be happy to chat more about the project at any time.
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Website Applications Developer - PHP/MySQL / HTML/CSS/JQuery/AJAX/JS / SEO - 10 years experience building front-end and back-end for a global yacht charter company. I was the sole developer for 90% of that time. I also built my own online yahtzee (dice game) community with real-time games/chat which is still fairly popular today.
Some of the projects I have completed: booking systems, search/sales/accounts/management/CMS tools, file upload handling, image processing (sizes, adding text, grafting two images etc etc), on-the-fly PDF creation, automated emails with files attached, web-scraping (with/without login spoofing), email scraping, financial/accounts calculations/reports, complex management reporting, proposal creator, editing responsive designs, real-time chat and AJAX-based games, community forum, paypal API, google maps, calculators, etc etc.