You will still have 20% equity giving you a safe cushion.  

My biggest concern with people who buy all cash are those that literally spend ALL their cash and lose their cushion when it comes time to deal with major repairs, increased vacancy, job loss or prolonged illness. 

If the factors above work in your favor, with a minimum of a 6-month seasoning period, it seems you could do this twice a year.3) is $100/month cashflow per property enough to to build up a cash reserves cushion?

Perhaps this is why you are saying cash out refinancing conservatively such that you can stay cash flow positive with a 20% reduction in rent, to give some cushion against this scenario?

Granted the expenses are factored in with an adequate cushion.  

This gives plenty of cash flow cushion for vacancies or lowering rents even in a downturn.  

If you can buy right with free equity and a cushion against market changes I suggest buy and hold.

I would just make sure it has the nice "backing" that should be moisture resistant and provide a slight "cushion" as well.

This is a great way to go since it makes helps the cash flow and gives you an equity cushion which opens up options for alternate exit strategies (like sell at profit) and insulates you from downturns.Finally, my observation from doing this over the last 12 years is that we are in a highly cyclical market and sometimes buy-and-hold is not the best, or even a feasible strategy.

Maybe this thinking is wrong, I don't know.Assuming I cash out, I'll still have 20% equity in the property (80% LTV on the new loan), which to me is plenty of exposure and cushion.