Hi Jay,Yes many obstacles and challenges.Indeed we corresponded a few years ago regarding some properties in Phoenix.

We have had a string of drug related robberies over the past month all ranging from breaking and entry to a mugging of an old lady going to her car parked in her driveway.   

Another issue is she told me she would send me back copies of all the papers I signed -- very clearly stated in her cover letter.   

I'm not a detailed person, so when CTL said it will hold all the documents, I didn't demand a copy of the contracts myself," Mr Ng said.That was the start of a massive headache.How the scheme workedCTL Group and its founder and director, Ms Clara Tan, were hot in the property scene between 2008 and 2012.Her seminars on topics such as maximising rental yield, spotting prime property below market value, need-to-know tips for foreign markets and the power of leverage saw robust turnouts, and were sometimes over-subscribed.Believing in her business model, several Singaporeans invested their hard-earned savings in her projects in Memphis and Indianapolis, where she said she "flipped" properties.When the US housing bubble burst and the 2008 banking crisis followed, owners in many US cities, including Memphis and Indianapolis, were badly hit.Many simply abandoned the properties they could no longer make payments for.

Its a roller coaster ride and a lot of work when you first start.There aren't any inherent advantages to investing in RE over other investments other than the hard asset, traditionally more stability, and the ability to leverage. 

As a recent podcast episode pointed out, the guest stayed in her place one night before she got sued for $10k.

I have been to costa rica several times and am aware of several vacation rental areas which are mostly weekly in nature.The biggest obstacle  I see is a property manager or service that handles the maintenance and the clean up from one weekender to the next.The professional ones typically charge a pretty good percentage of rent.

The footprint provides an obstacle in the way of designing the layout, but it's par for the course in our market.

Start there and see what obstacles you run into and let us know. 

@Michael Conte I know nothing about this maybe someone else can chime in here.