A major mistake when analyzing investment properties, however, is to rely on assumption when there are not many comparable rentals; I would recommend extending the search area, or finding a comparable neighborhood with more data.

If you have the deep pockets to pay cash, are familiar with the area and the property, and have enough $$$ to make repairs (estimate the worst case scenario), and the property checks off most of the "wants/needs" on your/your parent's list, go ahead and make your best offer.You could also call the listing agent and ask them if the seller has any special requirements that they would really like to see in an offer.  

I agree that "overpaying" for a buy and hold isn't the worst thing right now, especially if my renters are going to be paying the mortgage anyway.

Worst legislation in the country by a long shot.

But, if you have a significantly high salary that can regularly support paying cash for properties, that may not be the worst idea.

Those are questions for the listing agent.There are often mistakes in listings for rural/Ag property, so trust but verify what the agent says as far as ownership and acreage with the local County Appraisal Office online (if they have it) parcel mapper.

The worst experiences I've had are the ones that don't answer and drop the ball which delay closing and costs money/time.  

In our experience, the #1 mistake landlords make when selecting a Property Management Company (PMC) is ASSUMING instead of CONFIRMING.

But the adjuster advised us to possibly talk with the coverage department because it is likely that our insurance agent made a mistake while writing our policy especially considering the home is of somewhat high value.

If you did not get the security deposits as an adjustment at closing, you made a mistake, but you still owe those to the tenants.