I found a property in my area that would produce decent cash flow and appreciation; however, I would have to use funds from a HELOC on a different rental property for the down payment.

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.

If the price was right on Turn-key maybe, but probably more of the fixer-upper that can be leveraged later on for additional property or sold for a nice profit. 

Real estate is basically an income producing and or capital gain producing investment.  

If you are using STR, REPS, or self rental with material participation to convert to active or nonpassive income, you do not have to do this if you have passive business invesment that produce passive income that will exceed the loss generated by depreciation.

Purchase price: $80,000 Cash invested: $145,000 Turning a 3/2 into a 4/2 duplex for short term rentals.

Very happy with how it turned out.

What about evictions, 3, 5 months no rent then a rental turn, call it 10k total lose, for ONE prop, again negative cash flow.

I am currently looking more for turn key at this point.

That would be glorious...lol quite honestly to get a longer contract and have them turn into longer term tenants provided they are good of course.