The office confirmed with the owner that 66% of the balance due was a good gamble and we took the money.

You can gamble in Vegas, take a trip, buy a car, repave your driveway.

You cannot hold yourself accountable if a general partner has a gambling problem and decides he needs a lot of cash because Guido is going to break his legs. 

The answer is .. you are absolutely not.The only thing you are doing with letters, or mailers is blindly try to reach as many people as possible hoping you reach a motivated seller.That to me is not marketing, that is guessing, gambling.

If they are just selling to get top dollar they might be more willing to gamble and hope it appraises for higher and they are ok with having to go back on market.

It can be a gamble at that point, but if you've got that many inquiries, you'll likely get a good deal from someone that really wants it.

The loan processor Brittany Gamble was very attentive as well as informative throughout the loan process.

Either self-manage like many on here do, or hire an inexpensive offshore PM who works US hours & speaks eloquent English (that’s what I do).

Unfortunately with the limited knowledge and experience you have, you shouldn't gamble on making a deal without this information.

Would it be a good idea to take a gamble and invest in Oahu or is it the market already too high?