I’ve no idea what the most number of reuses I’ve done is but it’s going to be at least 3 or 4, with no issues.
The limiting factor isn’t really the olive, as long as you can slightly compress it each time to make the seal it’ll work fine, these aren’t high pressure systems. So that means the limiting factor on reuse is really the thread on the lever. The failure mode isn’t really “olive leaks because it’s reused”, it’s either “olive leaks because it’s not tight enough” or “lever body cracks because you had to try and compress an already squished olive”. (which gets more likely depending on how much of a gorilla you are of course, because the more overtightened it was the first time, teh more squished the olive is and the more pressure it needs to squish it more)