Strategies and Suggestions building a networks of sites.

Hi Folks... new here but not new per say. I'm in the processing of trying to transition from running a 10 year old successful web dev company to IM in an effort to relieve my dependance of clients and quit creating a product for a dollar.

The things I have going for me are:

1. Know web dev inside and out, html/css/php/wordpress/younameit
2. Known how to effectively locate and manage and outsourced team.
3. Have reasonable amounts of capital to make things happen.

Things I need to learn / weak points:

1. Have a few projects going / not fully sure where to focus the time I have (still very active in daily operations of dev house)
2. Do not have any track record of running any major seo campaigns and don't know the most efficient way to rank sites.

So that gives you an idea where I'm coming from. Now here is the premiss for one of the projects I'm working on that I want to share and get your feedback.

The main goal is to build the brand of a whitelabeled site I am running. I found a nice provider for the niche I wanted to be in that has a nice whitelabel offering. The bad part is that the site will not rank because it is essentially duplicate content of other whitelabels. As mentioned above our expertise is in design / dev. So I was able to make our versions of the product superior than most all of the competition. The site feels nice and converts very well. Once people find the site they come back and use it again. For the sake of simplicity let's say our product compares local pizza restaurants in cities around the world. So it has information about their pizza, reviews, etc. And allows visitors to purchase the pizza at which point I get paid.

So good news is that I have a site that is converting well and is in demand. So now I need to start getting traffic there. The good news is that I do have data avaialble regarding all the pizza places. So I can use this data to populate individual sites. Now while this is still the same content as on our main site and many other sites. I have done a POC for a small site targeting one city for with a domain like NewYorkPizzaGuy.tld (contains keywords but not exact match). I have then used the data from the main site and created some of my own content and gotten the site to rank on the first page of google. It is then bringing in leads which I send over to the main site. These leads are converting and even coming back and remembering the brand of main site. (I have co-branded the sub site as well).

Now based on the POC above I've started building an engine that will use the same template and allow me to import the data for each city and create a slew of sites. So the site generator is almost completed and will be working well. It will allow me do do things like tweak items which will then apply statewide to all the sites. So if I find out that something is converting better I can roll it out onto all the sites instantly... or A/B test across the network etc.

Now this brings me to my predicament...
I was able to get the first site ranking by hiring some backlink building, submitting a few articles to article directories etc. It was a fair amount of work and a bit costly. Furthermore the backlinks are not clean. I did not get any effect from Panda, but I'm a bit concerned that this business model is a bit "thin". Also even using low cost labor, link building is expensive and adds up. What I did for the first POC just does not seem sustainable. The link building was just too lengthy, costly, and probably not sustainable. So I have a few ideas and would love to hear yours:

1. I'm not affraid to create content. I have great writers and could easily start with say 20 sites and have them write articles for each on a continual basis.
2. Considering the above I'm not sure what would be best do to with the articles. Options might be:
   1. put them on each site to build larger sites.
   2. put them on a seperate blog I could create about Pizza in general which would then be adfree but be used to create backlinks to my network.
   3. submit them to article directories
3. Or maybe do a hybrid of everything.. make one site that has city sections as folders or subdomains and then put it all on one site.
   1. Problem here I see is that I'm not creating any backlinks myself
   2. I also like the idea of seperate domains as I feel in the serps it adds some authority to see NewYorkPizzaGuy.tld instead of yelp/nyc/pizza
   3. I also like individual domains as I like the idea of ranking them well and offering direct ads to the pizza joints. Again I feel like the NYC pizza shop owner is going to like having an ad on the newyork specific site... but maybe that is just me.
   4. Finally from a sale point of view I like having the domains apart as I could sell the sites for a region or country on their own.

OK well I think that gives an idea of the situation I'm in and what I'm trying to accomplish. Would love to hear everyone's thoughts