In your neck of the woods flood zone could be a concern that scares some away but not everyone will be turned off. 

I think I was just getting too fancy in my head and lost sight of the forest for the trees on this one.

And as @Glenna Wood said, there are other options that can be used so that your $100K in tax can stay with you.

As you can read above I have been ahead of the curve on this issue vs 98% of persons in the industry, formulating solutions and actions to be proactive vs reactive, I don't get scared I get to work and really that's the choice we have in life, climb up on a cross and cry or build a bridge with the wood and get over it.

For now, my sights are focused on learning as much as humanly possible and starting to network, which is something that would have been outside my comfort zone a decade ago. 

“Uncertainty” became a motto of coping and with little hope of an end in sight, I too hesitated.

You end up with not just mold,mildew etc but actual warping of wood, cabinets, trim etc. 

This picture is not super helpful to answer your question but if I were to guess I would say you either have no flashing or older wood bevel flashing outside and the caulk has dried out.

@Daniel Lozowy In terms of the roof I look at whether or not there are visible ridges from the wood under the shingles as this can sometimes mean there's a moisture problem or is simply structurally old, which increases risk of a roof looking.

I have sights on a property outside of city limits and ETJ, that is OU (Open Use) zoned.