If I buy this property and the money comes from someone else's account, will that raise any red flags within the IRS systems?

Lexington is good if it's over 275K they go much easier on you but I personally do the surrounding areas such as the Red River Gorge which has over 600million visitors a year and no issues with STR

Working with contractors can be extremely difficult as projects get delayed and there is poor communication(red flags were not present before project began).

Having "real estate investing" or "real estate" anything, in your LLC name will surely raise red flags for banks, especially as you move beyond net 30 accounts to larger credit lines.

This is a red flag for the IRS.

A whole sea of red flags waving, this is wild.

Nashville Yards is set to open in the Spring and the new Pinnacle tower is gaining office tenants like crazy - much to my surprise. 

Lots of red flags here with this property and location based on what's been shared. 

At that time for example Frisco was about 5000 people with one flashing red light. 

So, those who have been hit with there financing adjusting to triple and quadruple the money cost, slingshotted from life in the green to being deep in the red.