Primary issue I see is being priced too high for the current market by a few hundred dollars. 

Advice will be different on each path.2.

Use a payment processor to pay the original note and any wrap if there is a 2nd position secondary note that pays the seller the difference between their current mortgage and the total sale value. 

Your primary strategy should be to have the Contractor and all Subcontractors add you to their insurance policy as Additional Insured. 

Let me know if you were unable to download and I can email you a version in different format. 

Just make sure you take your policy to the brokers so they can do a direct comparison.Maybe hit up your primary home insurer to see if they offer a STR policy.

The financing and management of each are very different.

I bet if it were your grandmother or relative in that situation you would think differently.

From there every 20 point increment affect pricing differently.

If you choose to play with fire, that is your perogative.For your reference, here is a good primer.Here is the key paragraph:Rental discrimination is when a landlord or property manager treats an applicant differently based on the applicant’s inclusion in a protected class.