Downside equals Expense and they can be stolen easily.

That $500K could easily kick out another $5K in tax-free income per month.Combing the above two paragraphs $10K per month in tax-free income is the equivalent of $200K in W2 (highly-taxed) income.Mixing vacation dreams and investing usually sub-optimizes both.

We also note the date the property was sold and the lender can easily verify recording of the documents. 

One strategy could be to look for a property with flexible spaces that can be easily adapted for different uses (e.g., converting a bedroom into an office or studio).

(Easily 20-30 hours of tech time?

That could cause issues with a lawsuit though possibly easily remediable ones.

You can get a business credit card easily and get points and track business expenses easier that way.  

I only have a dozen but that easily brings in $20k a month in net income and requires less than an hour a month worth of work with a PM.

It is forgiving because it is easily patched up with joint compound and sanding.

I'm willing to pay for the service as I urgently need an attorney's help, but it seems like lawyers are not taking new cases easily.