What red flags should I look for that would lead me to see a property that has been sitting as an “unwise” investment

If they are not, that's a red flag.     

The more I’m thinking about this the more red flags I’m thinking of.

The beauty here is you don't have to necessarily choose which strategy you are embarking on for the first process of these strategies (buying a property in need of rehab and doing the renovations) - the best investors typically will have multiple exit strategies and can make unemotional decisions once the property is completed whichever way the numbers point to (flipping or keeping and renting/refinancing i.e.

Over the last several years casinos have went up, Ford Field (Lions) and Comerica Park (Tigers) were erected and people who loved the city began brainstorming how to revive it.More recently, Little Ceaser's Arena (new home of Pistons and Red Wings) construction started and is due to open Sept this year.

Yes, Charleston is beautiful.  

Several years before we bought a decade old nineteen foot Airstream, parked it on a gravel driveway below our house, plopped down some red lawn chairs and put it on AirBnb.

The beauty of this is you have a couple of great exit strategies when you're done. 1.

Purchase price: $2,400,000 A beautiful home nested in Paradise Valley Arizona.

Moving in and out of the current home could cause red flags for the lender.