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My question is... Is this a good approach or bad approach in attempting to improve the sites ranking? If it is bad, what is a better strategy? We have all these sites, so we wish to leverage them to boost each other up.
Any recommendations would be most greatly appreciated.
Unless you want to put the whole lot at risk, I would not go beyond that. Look at it from the SE's POV and think about what you'd do if you were them, and came across your network during a manual inspection. They're gonna take a good long look, at the very least. ;-)
If your going to link a network of 300 sites together its going to appear that you are trying to steal popularity from each one and gain important in a monopoly type of style. This will not go over good in especially google. If any of them are riding on the same IP location you will get nailed for that as well. My opinion is that you spread your network across hundreds of other peoples sites. You will get the best results taking your network of 300 sites and creating relationships to other sites and have those sites link to you. Then google will see your sites are popular across the board and give you some credit for your "true" existance in the web. Stay away from network linking your own sites together. IMO.
Site A has lots of deep links to site B - because site B contains explanations of terminology used on site A.
There are currently no links to site A from B
Site B has more traffic at the moment, but site A has more potential.
Is it wise to add a link to site A from the navigation bar of site B?