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Hey Cole, Good question. There are a couple of different routes you could take with the old or expired content. Leave as is, redirect to more relevant current content or remove it entirely from your site. My recommendation would be to redirect these old pages to the most relevant updated content unless they are receiving any significant amount of traffic. If the traffic is at 0 and the page is indexed, you are probably better off increasing the page authority of a more recent article or page by using a 301 redirect. You'll also want to ask what is the best option for user experience, it may be beneficial to have these posts in a searchable archive for users. There is a great article describing the options in a post on the Moz blog entitled "How Should You Handle Expired Content." Hope my recommendation and the article help you make a decision. Best of luck with organizing your site.

As long as you don't 301 penalized pages / websites to a non-penalized site, you shouldn't have anything to worry about. However, if you are sure your current site has pages penalized instead of a link penalty (which means that incoming links are not being counted, not that your site is penalized), then you shouldn't 301 anything if you are planning to "start over". There's been reports from people with penalized sites which moved to another domain and they were able to recover. I would only recommend such a move if you are now working only with your previous customers (existing before the penalty). But if you are still gaining search traffic and customers, then you should consider fixing the issues instead of moving. Just my 2 cents

Experiment.