Brie, yes we do IL Are busy with several closings at the moment.  

It's essential to recognize that all investments carry assumptions and risks, but informed decisions are based on historical data and trends.

So in the midst of any up or down real estate market, they are engaging in price discovery, and making sure they are investing at a heavy risk-adjusted value.

I suppose the lesson for me here is to validate across several sources, and to actually visit the area the area I'm planning to buy property in.

I'll share what I have learned in the markets I have researched.Ashford--this area has really picked up speed with STRs and there is a community in Ashford (Paradise Estates) that is investor friendly has several STRs.

The situation with the private lender is concerning and raises several red flags.

Im struggling because I do have one of the nicer looking homes in the area and a-lot more amenities but in my position I dont really want to take some major risk going into high season and missing occupancy.

@Frank RizzoYou should identify exactly what it is you are doing for him and make sure they understand that the risk is their responsibility. 

At the risk of bursting bubbles, most primary residences don't cash flow well as rental properties.

Start with a smaller property and gradually scale up your portfolio over time to build equity and minimize risk.