I believe he mentioned that his were rented to vacationers for a few months at a time so he had low vacancy, but he also mentioned that he could make more money by doing short term/weekly/nightly rentals. 

Are your short-term rentals marketed towards vacationers or corporate/relocation-segments?

Upon closing on my first 4 bed 2 bath home using the VA home loan, I've invested in furnishing my home for vacationers to enjoy and have had some success. 

I do believe I have the resilience to deal with student housing but I don't know if I'm sold on it, my question with that is during the three months in the summer, are the local landlords renting these properties out short term for vacation-ers, or do these units stay vacant until the students come back in town ? 

In some cases, you will have to do some forecasting as a lot of vacationers will book a couple months in advance so you won't be able to tell exactly what's filled up.

This probably goes without saying, but are there specific towns in the White Mountains Region that are more desirable for winter vacationers than others?

I was surprised to see many vacationers on the north side.

We do not collect any commission from you nor charge the vacationer any booking fees.

Most are renting their homes, not out of a desire to enter the hospitality business or make a killing, but out of a clear need to pay their bills and keep their homes even through the long winter months when there is no income but continuing huge expenses.Proponents of the tax believe that vacationers should pay to use town services.

I considered Gatlinburg a few times because I really like it there and it has year round vacationers but I cannot make the numbers work because the nightly rate is too cheap and there is too much competition, also it is on fire right now so good I avoided it.