Keep it simple to start, then eventually take on leverage to amplify your winning strategy.

So even if you eventually sell and do have to pay the gain 10 years from now that's only because you actually made money.

I am considering exploring converting a separate 2 car garage in the back of a duplex into an ADU.

Landscaping has the largest ROI (of about 200%), adding a wood deck or a patio will also provide a big increase in value (100% ROI).Add living space, consider converting attic space, finishing a basement, or repurposing a large living area to add a bedroom without expanding the home's footprint - this will give you an average ROI of around 75%.

When the area eventually becomes saturated or supply exceeds demand, all you can do is race to the bottom to compete on price.

I wanted to see if there was a legal way of converting the office to a short-term rental as well and just run 4 short-term rentals instead.

Eventually, you're out of the game, and blaming it on bad hands.

Plus, you don’t need squatters if you eventually own the property.

I'm looking into buying a $400-450K single family home to convert into a STR.

Look at it as a 20-30 year investment and it should eventually cashflow.