I don't think anyone is talking about flying these things into any environment worse than the risk of small arms (disperse your redundant systems and a bit of Dyneema around the soft pink bits) and MANPADS (IR aimpoint goes where?).
As for wind: I have not seen an HAV with a pressure cabin so we are talking low altitudes, where mean zonal winds can be around 30 mph max - not impossible with an 80 knot/90 mph cruise. Now use satellite weather planning to route around the worst of it.
I think there is a case for a tech demonstrator to prove out long-range cruise, operability and ground handling. Aeroscraft has done quite a lot on limited money, and HAV Ltd is working on the ex-LEMV. This actually is something that is being taken seriously in a lot of places despite the fact that there is not a lot of government money to be had, and that's a good sign.
Besides, you'll never see a heavier-than-air craft that, for some unaccountable reason, reminds you of Kim Kardashian.
