Has anyone been successful with roommate websites, etc

I haven't worked on it,but it is a nice concept.

How do you plan to monetize your site? Do you have any idea?

I just purchased the domain and I plan on using my own money to purchase the template, hosting, etc. hiring a webmaster to design it the way I want, and I also plan on selling memberships and using sidebar, banner advertisements. I also have a buddy who does SEO. I have somewhat of an idea as I have a few phone sex sites I own.

When it comes to selling ads on the site be sure to hit me up!

Not sure if this is sarcasm or not (I apologize if it isn't)but if not, I definitely will. It will be an alternative approach roomates though so I'll be looking for sites that pertain to that. I'll probably go through juicy ads or something. Of course, I need traffic before anyone will pay to advertise ;)

Not sarcasm.
No worries.
So,not a Mainstream site?

Well, yes, and no. Basically it's an alternative room mate site. Its a site where roomates who are in the adult industry can find a roomate who is okay with their "work" and lifestyle, or are in the adult industry themselves. I may even add a LGBT side of the site for those who are looking for a gay, bisexual, transgendered, etc room mate. I hope I'm not shooting myself in the foot here, but cam models, porn stars, phone sex operators, strippers, etc are usually secretive about where they work and what they do for work. So, why not find a roomie who's okay with your lifestyle? So, it's more mainstream imho. I might have ads that are adult related like sex toys, etc but that's probably as far as I'd go. Most of the advertising will pertain to those looking to find a room mate. Transgendered surfers/members might be interested in a surgeon ad or perhaps an ad for make up, trans clothing, etc.

One would think that a bunch of 40 guys who want porn start roommates would join...

True, but I think I can throw in cam to cam first time "meet up" and I definitely will not accept pervs who want to join just to room up with a porn star. Background checks and verification will also be site requirement. I mean, a 40 year old man can wish to room with a porn star all they want but everyone has a choice, and a block button. All it takes is for the site to have filters. Everyone will be able to filter out what they don't want, and what they do want and if they only wish for females ages 22-36 to view their paid listing, unless the guys deliberately lie about their age and sex, then that's who will be able to view their listing. I'll figure it out ;)