For a flip, you'll want to get a builder's risk policy, which covers the property during renovations, including any damage from fire, vandalism, or weather while it's vacant.

As Hurricane Helena went by, both of the roofs got damaged.

Unless it's obvious tenant damage you must fix things in the home. 

The downside is if it gets damaged you have to replace the whole sheet.

. $20K in reserves isn't a lot if something goes horribly wrong and there are damages if you default and he takes the property back.

If you are trying to piece everything together yourself remotely I think the time and brain damage and extra cost in time and cash you would be better to go yourself and do it. 

This is my first extensively water damaged home that I may purchase.

Don't quite understand what you mean.Wholesaling has nothing to do with where you grew up.Wholesaling (as well as any other business) is about lead generation.I didn't grow up in NYC, and if I were to wholesale there I would dominate that market with my ability to rank websites #1, dominate online presence, credibility, and competence strategies I can apply to my online image.I think this is why so many people are "afraid" of wholesaling.Break wholesaling down into its most basic elements.

I'd check for that before installing LVP and replace the subfloor where needed and treat any termite damage. 

But I draw the line when there is risk of damage to the property, annoyance to the neighbors, health concerns, pests, etc.