Depending on your income and tax situation you’ll most likely want to stagger the selling of rentals in hopes selling them all now doesn’t shoot you up into higher tax brackets. Keep in mind our tax system is progressive.
Planning is key here to determine your estimated income and how much gain or recapture each property may produce. If you’re working with a tax professional ask them to do a tax projection for you with one scenario assuming you sell all 5 today and the other assuming you only sold 2 today.
With the tax projection you’ll now have a good estimate of what your tax situation will look like and can make decision based on that.
Maybe you can consider selling your portfolio and doing an installment sale, this won’t help on the depreciation recapture but it would help spread the gain over multiple years.
Each strategy has pros and cons, if you want to rip the bandaid off an be done cold turkey (or warm turkey if you’re into that) there most likely will be a large tax hit but less headache holding them longer. Which do you prefer, less stress or less taxes?