Also, dynamic pricing could make sense if you're looking to have rent fluctuating.

It all will come down to the financials on these deals, and with a larger mortgage, expect less cash flow, so if I were your agent, I'd be focusing on making sure you have an income cushion but giving a broader focus on appreciation.

Seemed like they had the process down.  

You would need to make this clear to your potential guests when you advertise the rental.• Have no more than three bedrooms at the property, which would include the homeowner’s bedroom.• Be located at least 660 feet from any other short-term residential rental, as well as 2,500 feet from a resort hotel.• Be in a zoning area that allows short-term residential rentals.• Have written permission from your Homeowners Association (HOA), if applicable.

We thought about fencing/gating ours and making a community or just simply adding garages if it doesn't get too pricey.

Also, at the end of the day, if you have budget left over, make a draw and enjoy that tax free money. 

Recommend you find another insurance agent to either represent you or for you to talk with regarding making claims on your policy.  

Some of the headaches in this process:1) Duplex wasn't ready for inspection, even though Listing Agent had set the date. 

If anyone has any advice on this process or obtaining loans for this type of investment that would be very helpful.

You mention a $20k sale price and an agent can't really make a living selling at 6% of that.