Hi Weed,
I'd suggest an elder-law attorney to start.

A reverse mortgage approval requires a minimal amount of remaining equity. Granted, its less & less as the owner is older... but I'm not familiar with any approvals in an upside-down equity scenario.

An elder-law attorney will generally be well-connected with ancillary service providers who can help, but will know up front where your Dad's situation is protectable, and where he is vulnerable.

Luck!
Dave Donhoff
Leverage Planner

Can he get a reverse mortgage even though he owes more than it's worth?

No. There is no equity in the property.

What type of professional should I seek for advice on his overall financial situation?

Assuming he has funds for any professional, a Certified Financial Planner might be of help. They charge a fee for planning and advice only; in contrast to many other "financial planners", they don't depend on commissions for selling financial products. An annuity, purchased for the liquidated value of the other assets he is disposing of, will be one route you should be considering.

Thanks to both of you. I look at elder-law attorneys and CFPs. If the sale of his one property closes, he will be in much better shape financially. I hope to convince him to sell some of his other assets to keep him afloat. He's very stubborn though.