And even though he doesn't have to, he's still out there busting it out (@Frank Wolter, you need to take it easy a bit, brother - life is short and dollars are fleeting ;)  ). 

Just google New Orleans short term rentals and you will see how crazy it all is. 

Extended stay would be something like corporate visitors looking for a short term rental.Yes, we'd like to break even, get to use it a little each year hopefully, and one day retire to that property.

Just a few short months ago, my 2 partners and I created an LLC for the purpose purchasing buy and hold rental properties.

Short amort on this one still has a debt service coverage ratio of 1.25 at $1100 per month and jumps to 1.82 at $1600 per month. 

The downside is that the nature of project competition means you can get lower quality work and find a disconnect with those you work with since they are looking for more short-term work. 

That could be huge as I am fairly sure the Hawaii short term rental tax is high and it would not surprise me if some people ignore it.

For short term, (Profit / investment), which includes all your holding costs and rehab costs that YOU pay for. 

Long story short, I found a couple who had a wholesale deal that they were looking to offload.

Be careful with the short closing times, sometimes escrow can't get Title or the payoffs (if there's a loan on the property) quick enough.