I am contacting some attorneys right now to get more info.

I property manage STR in the cape cod so this is actually good info

In addition to the issues with debt costs, the properties don't seem to be functioning in a manner that will lead to profitability or even break even.

More info is needed to tell you if these are good properties.

From a tax standpoint, there are additional disclosures to make when selling a business asset for less than fair market value to a related third party. 

The additions are usually small.Buy focusing on real high value places, you are putting yourself in a narrower guest pool.

@Greg Scott this is the type of info that is pricelss and why i love biggerpockets.

I had one overall criteria and that was could I create additional value and could it pencil. 

I should add it will be a short term rental property. 

Continue with a viewing, additional questions, get applications, run ALL checks, and then make a decision.By being very clear about requirements, you will catch most early in the process and can let them know.