I don't like mixing the two - it can get messy if he stops mowing due to mechanical or health issues, etc.

Agree, Ring or some other camera monitoring  system, security systems will  have issues with alarms &  beeping and other issues which might be a nuisance for guests. 

Like "renting to section 8 tenants is actually really easy", "your agent is not on your team just connect with people like me doing hundreds of deals every day and use my team instead", that hood properties will have "15-25% net caps" for beginner out of state investors when in reality they will definitely lose money every month due to the rent not being enough $ to maintain a rental property, never mind all the tenant issues involved with this property class or the difficulty of managing them remotely... but he's done thousands of them just this week while sitting on the beach in Florida... 

I plan to put two duplexes on the property but with this high appraisal is there a smarter thing to do to pull that money out of it or just use it for better collateral for the construction loan most banks will lend on the transfer price within a seasoning period. we face the same issues for land entitlement and development.

Seems like this may be finding a way to force the depreciation issue....is there value in doing that? 

He and his wife also started another youtube channel where he talks about the political issues of the day. 

And yes, sometimes you have to pivot depending on other parts of your portfolio.The issue is that a flip is higher end finishes and amenities than a long-term rental so you could overdo the market if you have to rent it and get less of a return for the finishes.

One of the primary issues is the impact of rent control policies.

Quote from @Bob Stevens: Quote from @Henry Lazerow: In higher crime areas you can still find 1% but it comes with less actual rent collection/costlier issues.  

My other two will need a healthy $50k-$100k in fixes which isn't an issue but getting someone out there is.