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How many times..

Flats, sometimes... Rounds, never.
+1. Usually, once rounds go on, they stay on until it's time to change them. If they do come off, it's usually due to some maintenance issue and they go right back on. But even then, I often just time the maintenance to coincide with a string change anyway.
 
I've taken a set of GHS balanced nickels off one bass and switched them to another probably 5 times? No real issues but they were never exactly zingy to begin with.

I have a string trying and changing addiction, I justified it by saying it would keep me from buying another bass. I probably could have bought another bass with the amount of money I spent trying all the different brands
 
Did it several times with flats and rounds and never had any problems.

I just make sure I put them back in the same position, don’t back bend them and install them gently on the tuners.

So far, my Dunlop Marcus Miller stainless steel super bright rounds seem to be on their way to last forever !
 
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All the time. Sets I like come off and go in the alcohol soaking tube. (Denatured alcohol from the hardware store). And I might forget about them and they could be in there for months. I stick a post it note on the tube labeled with string set, estimated age, and the bass they came off.

If I’m experimenting with used sets, I might have to rewind the silk ends around an opposite rotation tuner, or barely have enough string to wrap the peg. That’s a riskier move, but if I’m careful (and lucky) it’ll work.

At this point, there are plenty of used, cleaned, sets for each bass. Which makes string swaps a breeze.

I’ve settled on a few sets that I use all the time, so there’s TI flats and light rounds for each bass.
 
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