It's more work, but in the past, I had good experiences, especially with travel nurses, doctors and affluent out-of-state skiers renting for a whole month or winter.

I was approached by people who are interested in leasing my property long term and use it for cooperate business travel accommodation. 

Maybe that'll give me more confidence to manage this second property remotely + increase bookings of my current place. 

Hey Alex, you need to be confident in the numbers that you come up with.

But I never acted because I didn't have the money, knowledge or confidence to pull the trigger. 

Even though the result was not favorable, I am confident that everyone involved in this transaction entered it in good faith.I can truly understand how this situation could be overwhelming for a new investor.

That seems to be at issue here and I'm confident in what I'm saying because this is what I do.

If you really want an answer you can confidently rely on you'll need to engage an attorney practicing in the state the property is located in and the state of residence of your grandparents and have him research the specific facts of the case.  

I want to be able to have the confidence when structuring deals. would i be correct if i said that COC % and preferred returns are the the main things that the investor needs to know about how they will get there money back?

What you need is confidence.