Maybe it exists but aside for rookies I know who have zero knowledge as to what they are speaking on, I have never heard anyone assume most flips are winning these days.

If the agent is their own broker and a sole practitioner then you need someone else to decipher the agency relationships that may or may not exist.

That would be best option as a traditional bank wouldn’t do this I read that I can assume the existing mortgage.

Would your STR business even exist without Airbnb?  

They will put it in your bank account. at a higher price, Airbnb is mostly crickets and booking.com continues to bring in good traffic booking.com has been very smooth and the whole review mantra with Airbnb is almost non-existent yes somewhat complex to set up.

Most of the ones I bought had existing tenants and almost all were paying below market rents and way below market rents.

So, if you put in 20K, you could set the bid up to the amount of the 100K total debt(80K existing + 20K additional) to ensure that the property reverts to you as the lender.

Human nature is fallible and any business that exists out there is run by humans.

Do you have any equity in you existing home (if you own it) so you can leverage a HELOC to use as an emergency fund?

There are a lot of other issues, but for you as the owner, the main one is usually do you have to have the current tenants out to build (no income) on to the existing property or are you going to do a knockdown new build?