Land Use attorneys are usually engaged for large, complex developments (although, again, maybe that's the norm in your market; I'm in California).

Depends they have expanding zoning regulations but mostly for ADU's and then its complex - same across most of the mid-shenandoah. 

Any tips for managing the complexities that come with wearing all those hats?

This is the part of the tax law that controls whether the money we spent on fixing something on our property is treated as an expense or as a capital improvement.The Regulations I mentioned are extremely complex and confusing. 

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As others have said, you need to look at the whole picture.Somebody buying an oceanfront property in Laguna Beach might be happy with a 2% cash-on-cash return, because they are banking on appreciation.Then somebody buying a 12 unit apartment complex in Cleveland might not do the deal unless they are getting a 15% cash-on-cash return because they are going to see very little appreciation and will need to deal with headache after headache.If just evaluating the cash flow, a cash-on-cash return of 10%+ is right to me.

It's the ideal thing to do if you need a very precise analysis, but I think AirDNA is still a nice tool to make parallels with a larger margin of error, even if you don't know much about marketing or any other more complex tools!

We have a 50 unit apartment complex and a local Subscription based Roadside Assistance company wants to partner with us to provide our tenants with unlimited priority roadside assistance services.

So he understands the living situation, that it's in a house, and not an apt complex, but he's excited about having the whole separate apartment to himself. 

Given the complexity of San Francisco and the eviction control measures that exist you do NOT want to do this on your own and need to make work with a landlord attorney to accomplish this.