Vacation Rental in Hawaii?

[Shanna Arthur]

Aloha,

I’m currently refinancing my primary residence to fund my second investment property. (First is a long term rental). I have found a permitted vacation rental on the beach that I like, but I fear that there will not be a high enough return in the immediate future. It’s a hard to come by condo of which I have been given early access to. I have lots of experience staying in vacation rentals and live within one mile of the unit. If I can rent the unit for at least half the month, the mortgage and fees will be covered. At this point in time most units in the building are already reserved 75-100% for the next few months. It’s going to be some work to get the down payment secured because my refi will take longer than the purchase. Needless to say, I’m a little freaked out because I need to see some return on my investment relatively quickly as I am the only one working (teacher) in a family of five. Am I crazy?  If the unit is rented full time, I could stand to profit $2000-$4000 per month depending on the room rate I charge. 
Mahalo for your thoughts,

Shanna