Thank you for sharing your thoughts on this important topic.

In case helpful, I've shared below a few additional points from the perspective of outside counsel:  one lawyer's experience at one law firm, never having worked in-house.

1. Issue Spotting. I agree that it is a real risk that an org doesn't know whether it is bringing the right issues to outside counsel. Having someone in-house who can issue-spot like this can be very valuable. It probably helps if that person is a lawyer, though I've also seen this done well by experienced operations folks who are not lawyers.
2. Giving Outside Counsel More Context Can Help. I have seen many occasions where an org comes to outside counsel with a narrow task or question but doesn't give enough context, and big issues are missed. This can be mitigated by keeping outside counsel informed of what is going on. In my practice, this often takes the form of outside counsel (i) attending all board and committee meetings and/or (ii) holding periodic check-in calls with the client. If you are bringing a large volume of work to outside counsel, they should be willing to do this sort of thing for discounted rates. For example, some law firms offer to attend regular board and committee meetings for free for promising venture-backed companies, though this is less common for larger companies and generally doesn't happen at public companies. A big drawback to this approach is that you are only getting the perspective of one outside advisor, and that advisor might not be best suited for every issue. Hopefully you trust them, and they will tell you when another advisor would be better or more cost-effective (they should!).
3. Oversight of Outside Counsel. I agree that, with in-house counsel, the workstream of interacting with outside counsel can largely be taken off everyone else's plate. I'd also suggest making in-house counsel responsible for engaging and overseeing outside counsel. Having one point-of-contact for a law firm provides clearer communication channels and makes the advice more cost-efficient. This ranges from mundane things like reviewing invoices to important things like ensuring you are receiving correct and well-calibrated advice. One useful tool here that orgs might consider is outside counsel guidelines, which you might ask any firm doing a significant amount of work for you to agree to. These typically describe practices meant to keep advice cost-effective (e.g., budgets and billing practices), but you can also use them to communicate expectations regarding the form of advice you prefer to receive.
4. In-House Counsel Traits. I agree with everything on your list of characteristics to look for. If I were to add anything, it would be ownership, organization, and responsiveness. These of course also apply to anyone working in operations. When I think of the best in-house lawyers I've worked with, these are the traits that come to mind first. In my experience, many of the items on your list flow from these (e.g., if you are organized and take ownership, you will tend to spot the most important issues and keep track of them well). I've also seen junior lawyers who excel at these three traits significantly outperform much more experienced lawyers.
5. Some Limits to In-House Advice. Even after an org hires in-house counsel, there may still be occasions when the org (or its board) needs to engage outside counsel directly, such as (i) hiring or firing a member of senior management and (ii) closed sessions of independent directors, including the minutes of those sessions and advice to those directors.
6. Privilege Protections. I agree with your characterization of privilege and its limitations.  Two small additions: privilege for in-house counsel can be applied more narrowly in some other jurisdictions, and privilege can matter outside of litigation, such as in a government investigation or when responding to a subpoena in someone else’s lawsuit.

I have a 4.5 year old and 2.5 year old.  On many dimensions it is easier now that they are a bit old.  We don't have to watch them as closely and they can play with each other (a bit).  If we are travelling or just need a break, they can watch TV (we try to keep it educational).   They are less fragile, so they can just eat what you're eating, it is easier to find a suitable babysitter and they don't need as many doctor's appointments, etc.  

But, other dimensions, they require a bigger time commitment.  The biggest one recently is that they are sleeping less.  A year ago, they would nap in the afternoon and we could put them to bed by about 7 pm.  Now, they don't really nap in the afternoons and sometimes they won't fall asleep until 9 pm.  

Thanks for organizing this. There is a lot of great content here that I've found interesting and useful.

I don't have much to add here, but this is a great question and one I'd be interested in more thoughts on. "Children Just Like Me" looks like a good book. My daughter also likes a book called "Be Kind" that was given to us -- it is about kindness generally and not effective altruism specifically, but helpful. It would be great to collect a list of resources on this topic somewhere sometime.

This is great!

Jeff, thanks for sharing these articles and your thoughts on this.