Main thing is to find out where his perceived risk is and what HE thinks will reduce his risk. 

This is the best way to ensure that you know exactly what you're purchasing.And most of the time, you can use the findings of that report to reduce the purchase price/get a credit at closing for way more than the ~$400 inspection report.  

Also, I'm looking for something to keep me busy as I ease into my retirement.You are trying to hack the primary residence part to reduce taxes and if you really can do it and you really live there then it will be fair, but if you deviate at all, the town will come for you and you will never get anything renovated if they think you aren't living there and it's not liveable.

Communication is challenging, most likely uninsured, but this is in-line with the budget.c) Keep searching for contractors, adding time to project and potentially costs.d) Buy scaffolding or rent scaffolding or a lift and demo myself for under $1,500, including dumpster.What would you do??

Sock that money in boring investments like index funds and focus on reducing your living expenses. 

The goal here is to reduce liability.Consult an Attorney for Liability Options: An attorney could advise on setting up an umbrella insurance policy to add an extra layer of liability protection.

In my market they keep reducing parking requirements while removing public parking.  

You can offer options like reduced rent during disruptive repairs instead of relocation; simply as a courtesy, but absolutely not required. 

This is where good tax planning really pays off—not only can it help you maximize these benefits and reduce your tax bill, but it can also help determine if paying for cost segregation is even worth it for your individual tax situation.

Residential, in my opinion, is a hassle so I am getting rid most of those properties so I can reduce my hands-on activities by 90%.