As for your negative cash flow situation, being in the red 900/month is not a good place to be in, especially considering an emergency can happen at any time.

Be suspicious of these red flags: any last minute changes just before closing, anything sent via email, anyone insisting on using their own title company or notary, any title company or notary that your closer/agent hasn't used before.

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. 

It was cool for me to see my roots.

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!).

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

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.

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