I know this is dinner time, they have a food truck there with pretty decent options. 

The only vacation rentals I see at the 55% occupancy range are bigger mountain cabins catering to large groups.I'd like to think that's because they're buying right.

Just some food for thought as you continue doing your research.

If not - I'm stuck renting for another five years or so (not the end of the world) to save up that cash, while still maintaining a sufficient personal emergency fund as well as a rental maintenance fund.Lots of food for thought here and I definitely appreciate everyone's input. 

I get a lot of mid-term rentals through Airbnb because I have my calendar set up to attract them and I set my listing up to cater to business travelers.You using your realtor network is a great way to get good clientele.

This is almost like saying you open a restaurant and need to make separate bank accounts for payroll, utilities, customers, taxes, insurance, repairs, supplies, food, etc....Learn to do some bookkeeping and it will make your life, and your accountant's/cpa's life much easier. 

We always have a speaker and have just started providing food and drinks as well.  

These are the people for whom 1 missing paycheck (for illness, emergency, etc) would mean not putting food on the table. 

As stated above, except for any food or drink you happen to order there is no charge to attend.

As stated above, except for any food or drink you happen to order there is no charge to attend.