Watch out for fine print that requires an additional fee at closing - this is a huge red flag and how most flat fee companies make money.

If you can swing hiring a PM without putting you in the red on cash flow even better. 

Going by the zestimate is a red flag.

I rent out on a 32+ day basis to avoid Chicago red tape and building restrictions.I own real estate in several states (strange that I'm still renting, I know!).

In that timeframe, the real estate market in the Riviera Maya has been red hot so this is pretty bad.The developers and the promotors of these deals (who get paid fat commissions to sell them) might be the only ones who will make (serious) money there.

The involvement of onsite management, often seen as a potential red flag, can lead to the property failing crucial qualification tests.

Ultimately the Red/Blue crap doesn't matter, it's about freedom.

The investor seems genuine and I could not find any major red flags about him online.

I bolded the first paragraph cause it's so damn true.

We advise landlords to require two main criteria:1) Household income should be at least 40x the monthly rent.2) Applicants must have a credit score of 680 or higher.It's also important to review credit reports for red flags like rental collections or high credit card balances.