Given this was a duplex in a developing area, my strategy was to buy and hold with cash flow.

If you normally buy and hold and flip one or two per year cause that exit strategy makes more sense you'll probably be ok but if you're primarily flipping and doing multiple that will be deemed as running a business.   

What are the down sides/gotchas for doing this strategy?

A Tax expert who can implement this strategy for me2.

@Vladimir Kunau Please clarify what your "exit strategy" is?

The only house I bought to live in will be fully owned by the end of 2024. Some facts of the house:Location: Nassau County, NY, Town of HempsteadYear built:1929Purchase price: 290,000 in 2013Condition: AverageLot size...

@Neil Ridens how are you finding your customers in this niche?

So cash on cash returns are easily 50%+ i believe this is what Airbnb strategy used to be before pandemic inflation hit.

Your job is to serve the customer first.

Where have you been finding success in the Huntsville/surrounding areas and what strategy?