I will preface this by saying I know nothing about the military so I apologize in advance for this question.

In the best-case scenario, you lose thousands every year in a market that is unlikely to see major appreciation in the next ten years.

I would loop in the real estate agent since it was his recommendation and not pay the rest as there is no contract.

I'm new to the eviction process in Chicago, so my first thought was TRIAL?!

But you're living in a market people are keeping an eye on from all over the east coast! 

Indeed, I'm not sure why you'd want to own a short-term rental home in Cancun to start with.People who land in Cancun (mostly tourists) generally either stay in a hotel / all-inclusive resort there or in the neighbouring Riviera Maya or they stay in a short-term rental in the Riviera Maya.

Investment Info:Small multi-family (2-4 units) buy & hold investment in Whittier.

@Jacopo IasielloYour best bet is to go to the top of the page under AGENTS and from there you will be connected with 3-5 agents in your area

I'm in the Houston area and looking to list my property as a midterm rental before going the traditional lease route.

Be sure to really dig into it, talk to others in your market, and make an informed decision.