I'd say the biggest reason is to have an accountable person you can turn who has not only errors and omissions insurance but a network of brokers, other agents, lenders, and title companies who are there to help make the complexity much easier and save you time and money. 

This discrepancy might indicate a complex market with varying property types and conditions.- Market Volatility: While home prices have increased significantly, the average home value has seen a slight decline of 0.4% over the past year.

We're going on year #5 with our rentals.It gets easier, and like you mentioned, life will become less complex.

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

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

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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. 

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.

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.