I currently live in Toronto, so I don’t believe house hacking would be possible, but I am aware of that strategy  

I’m interested in learning all different ways and strategies to find my own path. 

Look at any graph youwant, but just realize what really matters is what your "ONE" property is worth.5yr term isn't bad, but you need to have a solid plan to get that paid back.brrr is a great strategy, however, its difficult to pull off 100%. 

Primary reason for wanting to do STR is because I'm interested in gaining hands-on experience with this strategy so I can apply it towards longer-term goals in more traditional vacation markets. 

It is a banking and bookkeeping platform designed by real estate investors for real estate investors so it really does a good job of meeting your needs.

@Jaquon MillerA strategic strategy is necessary when investing in real estate.

This strategy yields higher returns in all metrics than traditional rental spaces.

The first thing to ask is your exit strategy on the second property - are you simply buying a rental or doing value-add?

According to our STR market studies villas, houses, and townhouses rent really well, I personally like the architect and the design of the Mar y Miel villas, I don't think paying double is the best way to go right now, we can help you sending you comparable properties so you can decide which is the best way to go and what options you currently have. 

I have seen more people torch their retirement plan using this "strategy" than I care to think about.As @Chris Seveney notes, an IRA can be setup with a specialty self-directed custodian so the IRA can be invested in non-traditional assets like real estate.