Holly, I strongly recommend using an experienced patent practitioner to help you pick a qualified person. Since you mentioned that your company has an outside counsel, ask that person if he/she is willing to help.
Considering everything you said, I would look for a practitioner with 5 years experience. In addition, that practitioner should have written at least 50 patent specifications and prosecuted over 100 pending applications.
Maybe this anecdote will help. I was occasionally involved with training a patent agent. In his first two years, he wrote about 10 patent applications and prosecuted about 15 patent applications. At the end of those two years, he convinced a company to hire him. His rationale was that he would be cheaper than the company’s outside counsel and that he knew what he was doing.
He used me as a reference. I met with him and told him he was not competent to do the job. (That didn’t go over well.) I called his boss and reluctantly recommended him. His boss told me that he (the boss) had no IP experience and was relying on my recommendation. Knowing that, I stated that the agent should have his work reviewed.
The agent convinced his boss his work didn’t need review. Upon occasionally talking with the agent now, I’ve learned that he has made some big mistakes. His prosecution is average at best, and his company is not getting the quality work they should/could be receiving. In addition, they are substantially overpaying him.
What’s the point here? Neither the agent nor the boss know that a better job can be done. That could have been nearly eliminated if the company had relied on an experienced practitioner to help select for the job.
Good luck!