Respect their time by giving them the information they need to include or exclude your listing quickly, and then earn their respect by answering all correspondence quickly.Making life easier for the frazzled person trying to do their job is its own reward.

Not every investor is willing to take on properties with these kinds of challenges, but if you can make it work, the rewards are huge.

It will have ups and downs, you will make mistakes, but I have found real estate investing to be a rewarding endeavor. 

They say it’s too much stress, too many surprises, and not enough reward.

However as you correctly point out this is far more risky and or its risk capital compared to buying a income property.. but the reward can be strati-spherically higher .. not just a little bit but it can be life changing profits on some of these deals.

With the numerous investors on this forum they have done this to, it is probably just the tip of the iceberg. 

May your bookings be as plentiful as you wish, your guests be low-maintenance, thoughtful, and honest, and your positive reviews numerous.

As you mentioned, it depends on numerous factors, with pay history being a big one.

It seems these inevitably run into problems as the investment projections are not met, loses begin to pile up, SEC compliance issues are ignored, and numerous legal actions are instituted against the sponsor.   

I agree with @Connor Hibbs's comment on terms for first time flippers and if this is something you want to start doing more frequently I'd look for lenders that offer some type of rewards program to gain better terms through doing repeat business.