If they are professional, they can explain this quickly and easily.

Saying that you are not handy in the least leads me to believe you could easily be snowed by bad subs and thus should have a good GC to look out for your interests. 

But new folks on this site can’t easily differentiate which replies are most relevant to them.

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.