For example, wood rot is not covered in most policies.

This is a more general term used by some insurers to cover all lenders.

They'll typically require ~10% down and then cover some or all of the rehab.

But I am also having a lot of booked guests concerned about their upcoming stays because of the two storms currently brewing.I've thought of self-insuring but I've been able to find policies with good coverage that also cover the loss of income.  

Also, I've added about $250 to my monthly costs to cover utilities.Looking on Furnished Finder, I do see plenty of places in my approximate price range, so I thought my target (average of $1100/room) was competitive and reasonable.

This can provide you with the funds needed for a down payment on your new home.Rental Income: Keep in mind that the rental income from your current home can help cover the mortgage on your new property.

Or, is it worth just getting an umbrella policy to cover all properties?   

I have been able to find companies that will cover real estate portfolios on one policy in other markets but no luck in the Florida market.

Most also cover cleanings between guests, but don't handle maintenance.

They can ask you to serve notice so one unit (or both) are vacant at the time of possession, but if you agree to that make sure you have a large deposit and some of that is not refundable if the buyer backs out as you will need it to cover the lost rent.