I know or know of people in your same position (executive level tech experience + capital) who have done well in this business, and also ones that have imploded in a spectacular ball of flames. 

New construction codes would require the construction of a house that is more resistant to high winds and will have a new roof.   

I always suggest seeking the path of least resistance.

I couldn't resist taking these pics as well...the tenants cats had torn down all the curtains & literally shredded the tenants couch but $$$ on-time :) 

With such a great cash flowing property, I would be very resistant to selling.

If the bottom stair is taller than the top stair the basement may have been designed to resist water. 

Although this is probably less likely than the water leaking in through the window wells, it is possible, and you'll want to eliminate it as a cause of the flooding before deciding on how to fix the issue, because if it's groundwater, then the solution to the problem may be completely different than if it's water coming from other sources.As you consider these questions, keep in mind that water follows the path of least resistance--for example, water will flow through a gravel-filled trench much quicker than through solid earth/clay.

The resistance is those territory owners of the "old guard" who have literally everything to loose.

It all comes down to what the investor's goals are, and what is the pathway of least resistance to get started! 

Nature can be a great asset, resist wholesale clear cutting!