I know the handrails are not the correct height for modern times, but if they were higher on the landing no mattress would ever make it to the bedrooms. 

Will definitely take that in to consideration!

Bought house new for 300K in 2006 at the height of the real estate boom. 

However, my experience with Home Warranty Companies varies considerably.

As a result we started ours earlier than if our only consideration was asset protection.

That said, your chances of damage due to hurricane / tropical storm remnants look to be considerable, especially with what we've seen this year.

Then again, you really have to consider your options - which can be largely dictated by the lending institution's criteria.Another thing to take into consideration is how you plan to manage the tenants.

If I had somewhere for my family to stay, I'd consider selling my primary since its gone up in value considerably since I bought it 9 years ago.

Any particular considerations to think on? 

Thank you so much for your consideration, we greatly appreciate it and I look forward to hearing back from you!