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.

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

Predominently focused on multifamily and medical office syndications. 

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. 

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.

I have been airbnb’ing it less than 120 days which was helping me to work/ travel a portion of the year outside of LA -  not worrying about the paying both rent and mortgage at the same time.

My total of all annual expenses is about $220K- everything, insurance, haircuts, leisure travel, property taxes, etc all included in thereI dont want to semi-retire any time soon, but I think it's smart to have long term plans.

I just graduated with a degree in Cell & Molecular Biology and my plan has been to go to Medical School to become a doctor.

But one or two may decide to take the plunge, and try the path less traveled.

My assumption is $0 rent those months other than a holiday week like Thanksgiving Christmas and Easter, where the projections are showing thousands per month.As a frequent traveler to the area, I cannot imagine much rent revenue in Jan, Feb, March, April, Nov, Dec.