A few of my red flags: He didn't call me, she did. 

I agree with the answers above and that condos have a lot of red flags for STR investments.

Less governmental involvement, restrictions, fees, red tape, etc. here in SW Florida. 

The company red tagged it.

The property is the clock tower at 111 NW 2nd Street, Stuart, Iowa. 

That right there is enough of a red flag for me.

In short, if you're not renting every week of July-August and every weekend of the winter, you're taking losses, particularly given the ridiculous prices I'm seeing new investors pay farther north in vacation areas like North Conway or the White Mountains.And looking solely at North Conway's recent court case is a red herring: plenty of small towns around the NH continue to enact knee-jerk reactions and excessive permitting/regulations as a reaction to STRs assumed role raising housing prices and shrinking supply for local residents.

I'm sure there's money to be made there in real estate, but it seems to be heavily reliant on one industry (Army) which is a red flag for me when it comes to evaluating markets. 

I know that comes with much red tape with the different zoning laws.

No delays, no red tape, no custodian transaction fees each time you perform a transaction.