Given Dave's experience and track record of high-quality work, and his proven maturity, skill, and competence, there is no reason not to allow him a high degree of autonomy: he knows how to do the work, and he doesn't need someone telling him how to do it. The company's stricture against working from home is expressed as a preference, and concerns quality issues; this is a pretty clear-cut case where this preference can be ignored. Dave's record makes it highly unlikely that quality will be an issue, and he has a good reason for wanting to work from home. You can always check the work for quality later, if necessary.

The report, on the other hand, is a different matter. It needs to be done a certain way, and it's going to the higher-ups. As such, it will reflect on you at least as much as it reflects on Dave. Furthermore, on the basis of the limited amount of information we have about him, Dave's communication skills may not be all that great, and he may not take...