Your realtor will be able to give you a much more detailed market specific answer but with house hacking and a VA loan it should be possible to get 0 out of pocket.

Every market can be invested in successfully.

I would rather invest in safe markets that produce a good return, then I can use that income to pay for a vacation anywhere in the world.I'm very pessimistic about the STR market in Hawaii.

When I worked with a property management company, we had someone buy a unit (single family) that had a STR and marketed it as a STR.

If you are having other investors to steer clear that might explain why the property is still on the market. 

Then to find inventory, you need to search out, i.e. network, and find out who is creating these type of notes or you help people that may have an interest in seller financing how to create a note that is marketable to the secondary market.

If we are losing money every year, but do plan on holding on to it long term, with our goal being appreciation of the market and someone else paying a good chunk of our mortgage, is this worth doing on any level? 

I signed up for their investor profile because I am interested in the appreciation in the North Texas (or northern suburbs of DFW) market.

Very solid market, been investing there over 10 yrs and the rents continue to climb! 

This setup ensures every project stays on schedule and within budget, which is huge in a market where timing is everything.3.