I currently have a single family home as my primary and two investment properties.

This home was located in a zip code that is notorious for its ultra-modern design (though those homes are still sitting for sale).

Leverage  anything in the US  so you can  use the cash to buy in CR  ( US home / 401K / other assets ..etc)  ...pura vida !

I find that the best deals on the market are usually newly listed (less than a week on the market) and usually the deals that haven't sold have significant issues with them.What are the reasons that you think homes sit on the market for a long time and how do you navigate the issues to make a deal that works for you? 

If you haven't checked the market for homes with "inlaw suites" or whatever your market equivalent is that can be a way to get it done as well. 

Is it legal to offer to rent the property back to the homeowner who already lost their home to foreclosure when negotiating the redemption rights purchase? 

Consider starting small by house hacking a single-family home, renting out rooms, or adding an ADU if possible.

You purchased the home as your primary.

Basically, you can't STR an entire home here, or even an ADU, and can only STR out a portion of a home that you reside in.

Focus on smaller single-family homes, condos with low HOA fees, or multi-family properties in these regions, and build a reliable local team of agents, property managers, and other professionals to ensure a smooth investing experience.