For me, it's more a case of renting a super once every 1-2 years. Over the seven years we've been doing Alaska cruises, the IIs came out (so if I'd bought back then, I wouldn't have a II).
Every so often, I just open up the LensRentals website and go through their lenses for rent, and open up a browser tab with every lens I might want to buy. I then go through a "tab sorting exercise" to decide what order I'd buy them in (you know, if I won the lottery but insisted on always using the same credit card just as fast as I could keep paying it back down to $0 so I could get lots of FF miles...), and too many supers are in the running for me: 300/2.8 (silly to not own something faster than f/4 if I'm going to buy a 600/4 someday), 600/4 (because our not-yet-created children are going to play soccer, dammit!), 400/2.8 (because once you have the 300/2.8 and 600/4, the 400/2.8 comes next and the 300/2.8 collects dust except for those times when 400mm is too much, right? - but the 400 is too much to buy before the 300 and 600), 400/4 DO II (because I'll deal with the few shortcomings if it means I have a lightweight super, and my wife will probably want this one), and then the 200-400/4/1.4x (because a 24-105 and 200-560 combo would kick ass). Considering that there's also a 200/2 on the list, a shit-ton of Zeiss (85/1.4, 100/2, and 135/2 specifically for my headshot photography, plus 35/1.4, 35/2, 50/1.4, 50/2Macro, and maybe a 15 or 21mm), some tilt-shift (the 90 and maybe the 135 specifically for my headshot photography), and of course the 85/1.4 IS, 24/1.4II, I can't bring myself to buy a 600 (but should I buy a 300/2.8 first???) and therefore delay so many other smaller-ticket items (and we haven't even cracked the wishlist of more Profoto lighting stuff...)
In the grand scheme of things, I'm a believer that as much as I plan (dream) out my future lens purchases, the only thing that matters is what lens should I buy next. We're definitely off-topic here, but business aspirations aside, it's the 24/1.4II. We've already got the 14/2.8II, 35/1.4II, 50/1.2, 85/1.2II, 100/2.8L Macro IS, and 135/2. We frequently go to Jazz Alley in Seattle, which allows non-flash photography freely. When we sit close, 14 to 35 is too big of a gap, and the light is IMHO too low for a 5DsR to survive on a 24-70/2.8. From a business perspective (I hope to launch a side business doing headshots in a rented studio space as soon as 6 months from now), I want the 85/1.4 IS for the focus speed and optical quality I'm led to expect; I use the 100/2.8L Macro as primary, but want to have an 85 and 135 prime handy, with a 70-200/4 as versatile backup. After that, it's either a 200/2 to give me a long portrait option, or start going for the Zeiss Milvus 100/2, 135/2, and 85/1.4 to see what it does for my headshot work.