There is no perfect software out there.

If he has the income to support a $550k mortgage, and a healthy cash reserve fund, he should invest the money.

Not all attorneys are equal, so ask them questions to find out how often they do this, their methods, their success rate, etc.

From what I'm reading the medicare lien will be wiped out after the foreclosure, so I'm wondering if medicare will negotiate with us. 

Certainly reach out to him for expertise.  

I have a pretty big chunk of cash sitting on the sidelines that I would love to deploy to start building long term generational wealth. 

Purchase price: $350,000 Cash invested: $74,000 Purchased this 28 unit RV & Boat Storage facility in Missouri. 2023 construction - 100% occupancy at purchase.

You will likely need access to six-figure cash or loan to execute your plan before your long-term financing.Can you piggy back on the seller's bigger project?

Of course, with all things, the answers to all these matters will depend on the circumstances.California tends to have more laws on the books and requirements and restrictions that it can be a good idea to form a CA LLC for out of state property so that you as a CA resident are covered, and to try to have your contracts fall under the purview of CA courts.

Appraised value is going to look at comparable based on distance...while the market may value 2 properties, literally across the street from each other differently by hundreds of thousands of dollars.Investors for decades that do cash out refinances, or BRRRR as we now call them, have known this for decades.