A lifestyle that they can travel frequently and for longer.

@Forrest BrownWeight in the factors of investing out of state with travel, time, and energy to invest. 

Are you comfortable traveling in circles of people we have this kind of cash available.

Buy and Hold: Norfolk (Best Cashflow Potential), VB (Townhomes tend to work well, Green Run is a great area for cashflow), Chesapeake, Newport News, Suffolk (Less Military presence which is why i would put last.)STR: VB (in the proper zones if you have the money $850K+), Norfolk(Ocean View area specifically but have to watch out for the AICUZ restrictions), Leave the restPart of that decision process is distance to that I would need to travel to deal with rehabs, I hate dealing with the tunnels so I would almost always pick places on the peninsula last since I am based in Chesapeake.

Kept in its antique 1960s interior and displayed classic Disney designs for travelers looking to stay for Disneyland

These places will be more expensive, for a reason.Now I do think that there is some opportunity in certain areas of upstate NY for short term rentals, however upstate NY is not a well established travel destination so your occupancy will probably be low and highly seasonal but this method is viable.

Plans to were announced last month to invest $2B into the cities airport in anticipation of the population/business travel growth. 

Would all travelers be OK seeing this setup or could you get dinged on a review?

Even if my place would get known some way, I still face the problem that Montrealers will rather rent a place in the Laurentides, which is an established market, where there is more stuff to do and, most importantly is much closer to town, as people don't want to waste part of their weekend traveling long distance.

No pool needed.As a frequent mountains traveler I will not consider a unit with no view and no hot tub.I am not experienced in Charleston, but from what I know these would be extras and probably not essential for renting.