Once you have some leads coming in, you'll start to see patterns in what kind of traveler is looking for your place(s).

Short-term rentals can be a great starting point, especially in markets with high tourism or business travel.

Seasonal Slowdown (With a Twist)The holidays always lead to a slower rental market as potential tenants prioritize family, travel, and gift-giving over finding a new home.

DO you want to do mid-term rental to traveling nurses?

I (barely) watched some of the podcasts cause BP shows up on my youtube feed when I travel. 

Common deductible expenses include mortgage interest, property management fees, repairs, and even travel expenses related to property management.

To me STR and hotel caters to different groups of travelers and so despite competition as long as the travel demand of Hawaii remains (as you pointed out is a robust assumption) I think both will continue to do well.  

I'm doing quite a bit myself but the cast iron part is a job bigger than I can handle.Any recommendaitons for rough-in plumbers in NJ and willing to travel about 15 miles outside of Newark?

A mid-term rental could be an great option during the 6-7 months you're away since it appeals to traveling professionals, remote workers, or individuals relocating and offers stable income without the constant turnover of short-term rentals.

He currently travels often for work and resides in TN.