Also, I noticed his office has poor controls over sensitive data.

However, a lot of concerns can be mitigated with looking at their past rental behavior in a lot of different settings.

You can have an email for each account and you should be able to set your phone up see multiple accounts at once should you get inquiries or messages.Just log into each account to make updates and price changes.

Unfortunately, I do have a property in an HOA, which often comes with their own set of rules that you'd have to follow of course. 

I wonder if the change of density could off-set cost of underground enough to make it make sense.... 

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Let me know if you need any tips on working with contractors or setting expectations.

They're basically two different skill sets and it's fallacious thinking to assume you can do one because you can do the other.

Also being able to write down/document goals I set earlier and see if they are being hit.

The real work is locating these properties and I've learned the best way to do this is to work in towns/areas that have online GIS systems that map; topography, wetlands, soils, etc. and assessors data available for download either from local sources or listsource.com.