At those costs it would take me about 12 years to break even if there were no other expenses for either unit during that 12 year period.

For example, garage disposals, tenants don't think about what goes down there and how it breaks or mess with your sewer lines.  

Smart locks break and screw up all the time.

Just make sure that when doing this house hacking strategy that you run the numbers to make sure you will cash flow or at the very least break even upon moving out.

I am doing this completely remotely, which has been a massive pain/lesson learned (topic for another day).I signed a very high-level agreement (i.e. expectations simply say "drywall and paint") with him for drywall and paint work at my home for a total of $10KI have paid $5K as a down payment as well as ~$2K in materials over time, as neededThere have been multiple break-in's in the home, and he has done me favors of working with the police, and boarding things up.

As a rental, if you can’t rent long-term and at least break even when you refinance, it’s not a good deal, too much risk there.What are your holding costs looking like?

Miami Beach is going to be a tough market to break into based on money, so your network and hustle will put you in the right crowd.

I printed and hung up that picture as motivation to keep pushing toward the dream of breaking free from that reality. 

However, after reflection, I realized I was becoming too emotionally attached to my first investment after a 15-year break and faced challenges finding reliable contractors.Update (5/17/23):After three failed contractor attempts, I finally secured a reliable one.

Consider the potential for tax breaks based on your interest payments and any expenses you may incur for the building that you can write off.