When you look at Pittsburgh more specifically, you'll find that the region has some of the very best medical research, healthcare systems, and universities in the country.

Any signs of previous problems being covered up, or band-aid repairs?

Don't be intimidated by his idle threats or fear that he will enlist the aid of his parents.4.

But you are just using estate planning and LLC's to work in the modern era to fight modern wealth destruction (law suits/judgments, healthcare expenses leading to long term care / incapacity, remarriage after death, death or remarriage of children.) 

They are getting to the point where they need around the clock care and need to sell their house  where they lived to help pay for the health care and living expenses .  

You try stuff and if it fails (and aren't wiped out), you learn from your mistakes and try something different.Now the question becomes the best ways for me to increase my passive incomes to create this income stream I need (the wellsprings of cash that outrun my growing expenses [healthcare in old age] and inflation).

We are both currently in healthcare.

The industrial and healthcare industries in Temple are constantly growing and the city is expanding like crazy. 

Make sure you figure in Health Care.  

I did however contact the Vermont Legal aid offices on two occasions and both lawyers said that we should just split it as it was not worth the cost to litigate this and the issue falls into a " grey " area of the Vermont system.