I find it easier this way once you know your regulations and ROI in certain areas.  

This option is ideal for penalty-free investment but comes with added complexity and strict IRS rules.Alternatively, a 60-Day Rollover allows you to withdraw funds and redeposit them into an IRA within 60 days to avoid penalties, though it carries the risk of missing the deadline.

As more people placed more properties in STR inventory, and as more municipalities taxed and regulated the industry, the profitability of the overall industry has reverted to a much more aligned (lower) risk adjusted return.  

However, there is no specific holding period contained in the tax code or regulations and there is no "safe harbor." 

Companies avoid locations with high operating costs from taxes, insurance, and over-regulation.

Each state has specific regulations in lending for Private/Hard Money (*Texas*).

This vary heavily town to town. 20% down is great if buying strictly as investment but if you have a way of owner occupying I would explore that route and apply the 20% down to increasing value of property and instead using low money down loan. 

I'm dealing strictly with the sellers themselves. 

I know in my area they can require it, and we are nowhere near as strict as NY. 

If you're looking for strictly cash flow and that's the most important, I definitely recommend going with Cleveland.