We will rely on my husbands income when we move, although, I will start looking for jobs a month or two before we actually move.Given our situation, would it be more beneficial to find a short term rental (6 months or month to month lease vs. 1  yr) when we make the move from San Jose to SD? 

The LL certainly takes on a greater risk upfront, but if the business is able to deliver on the expectations set forth, it can be very beneficial to both parties.I've been following this contract model for a some time now, however I've yet to find any applicable discussions on this topic that one could actually put into practice.

Is it ever beneficial to move tenants around within the building in order to rehab each unit and try to get the whole place renovated more quickly?

It will definitely be beneficial if you decide to market your properties toward military personnel.

It will make the overall mentor experience much more beneficial and worth your time and theirs. 

From your post, it sounds like BRRRR and buy-and-hold are mutually exclusive; is that true?

Or make them mutual or limited in other ways.

Look up parole rule for real estate contracts.Almost always they need to be written and mutually accepted to be enforceable.Gee, another reason text messaging isn't very effective.

If so, was it beneficial?

It is not worth his trouble.As appointed administrator I understand that it his job to do whatever is most beneficial or the estate.