Not dissimilar to the old Forum:
Best Swim: IM Austria
Best Bike: IM70.3 St Polten (now Challenge)
Best Run: IM Hamburg
Best kit bag: Outlaw (Blue Seventy)
Best Finisher Shirt: (Outlaw '17)
Best Medal: Hmm that’s difficult
Best for family/supporters: IM Austria
Best other: Cotswold 226 (lovely pottery finishers mug & medallion)
Worst Swim: Outlaw (bit harsh maybe)
Worst Bike: IM Hamburg (relentless, soulless, no support)
Worst Run: Outlaw (boring 4x lake)
…and so on
Best Swim 70.3 Florida Disney . swimming in the lake at Magic kingdom
Best Bike IM Regensburg loved the long climb up through the forest
Best Run . IM Frankfurt so much support
Best supporters IM Frankfurt
Worst swim . 70.3 Lanza . ended up doing some walking it was so shallow
Worst bike . 70.3 Florida just plain boring . v fast though
Worst Run . 70.3 Florida . not so much the course but the humidity
Best swim: Cozumel. Plop off a pier, 2.4 miles tracking along the coast in crystal clear water, loads of fish etc, tide assisted, not even a turn buoy.
Best bike: Cozumel. Flat, fast but no drafting, scenic, some windy parts to keep it interesting.
Best run: Italy. Lovely clip round the harbour, through some squares and leafy shaded shopping streets, out into a park for a quiet bit, repeat x 4.
Worst swim: Bolton.
Worst bike: Italy/Barcelona tie. The drafting did my nut in.
Worst run: Barcelona. Either soulless road to nowhere or way too congested.
Medal: 70.3 Worlds 2013 - like a dinner plate
Supporters: Tenby.
Finish line: Frankfurt
I am doing this sort of exercise at work; so in the zone now!
Do you reckon we could widen it to rank all the events?
At present its binary as best or worst
What about taking various events and ranking on 10 criteria:
Course quality
Ease of logistics when there
Travel cost
Standard of competition
Etc etc?
Best Swim - Tenby
Best Bike - Austria 70.3 (St Polten)
Best Run - old Forestman course
worst swim - Bastion
worst bike - Midnightman
worst run - Midnightman
harsh on the midnightman as its actually a right laugh but taken on their own merit multiple laps on a trading estate is grim as hell but the people, the organisation, the overnight factor makes it the most fun Ive had in an event behind Forestman
best support - Tenby
best medal - probably Austria 70.3 still
best t-shirt - Austria 70.3, Zoot still going strong
Best Swim: IM Wales 2011 (the lumpy one- got a PB!)
Best Bike: IM Florida
Best Run: IM Florida
Best kit bag: IM Switzerland 2005 - still use it!
Best Finisher Shirt: any of the REP event ones (Worthing Tri etc)
Best Medal: not tri - Toughguy horse brasses
Best for family/supporters: IM Wales
Best other: Outlaw
Worst Swim: ITU LD Champs, Almere, 2008 - the overlong swim course
Worst Bike: IM Austria - full on cramps most of the way
Worst Run: IM Austria - suffered after the bike leg
Ha, I don’t think you can blame the course for your physical woes 
Best Medal: LCW
Worst Swim: Outlaw Holkham
Best Swim: IM Austria
Best Bike: IM Lanza old course
Best Run: IM Nice
Finish Line Announcer: IM Nice
Best kit bag: Any IM over the 5 years prior to 2019 version
Best Finisher Shirt: Lanza 2013
Best Medal: IM Austria 2007 (my first long distance)
Best supporters: IM Wales
Worst Swim: Roth
Worst Bike: IM Bolton latest incarnation
Worst Run: Wales (too damned hilly)
Never Go Back: Bolton
Oh best Finish: probably IM Hamburg too…got a High 5 from 2007 ITU World Champ who was compering; Roth was in a thunderstorm & almost deserted when I raced, but it would have probably been the best on a dry day!
Most impressive logistical effort: IM Hamburg. Bike course would have been better suited to the US President escorting a Bullion shipment…as it meant no spectators on the bike course, it was so well closed-down.
Hamburg really was a great event, apart from the poorly chosen bike course imho. 115 mi long, and just too boring/lonely & dangerous in places.
“Hamburg really was a great event, apart from more than half of it being totally shite”.
Best Swim: IM Austria until you get to the canal and then it could have been anywhere as it all tastes sh1t
Best Bike: IM UK Sherbourne - hills, Cerne Abbas, dead animals and porn mags at the road side breaks the monotony
Best Run: Challenge Iceland
Finish Line Announcer: Roth
Best kit bag: Any of the IM Switzerland bags
Best Finisher Shirt: Challenge Iceland Hoody
Best Medal: TS M40 Gold Cross Triathlon (only National title I have won)
Best supporters: RedBull arch IM Switzerland - pretty obvious when you have seen it
Worst Swim: ETU Challenge Rimini or IM Barcelona
Worst Bike: IM Barcelona - blatant draft fest
Worst Run: IM Barcelona - you cook from the heat off the tarmac and the buildings
Worst Finisher T-Shirt: Any of the 70.3 Polo shirts with massive collars
Never Go Back: Bolton or Italy
Well, when you put it that way 
Most sorely missed: 70.3 Wimbleball.
(And the Spring Ballbuster)
Best swim: Swanage
Best bike: alpe de huez long course
Best run: there’s no such thing but Budapest AG champs had good beer, so did alpe de huez
Another good race: immortal stourhead, amazing setting.
Worst race: anything involving DNF (2 ever, both due to bike mechanical / bad kit prep)
Did that one too IMUK Sherborne & the dead animals were indeed unparalleled
Hmm.
Best Swim…Lanzarote.
It’s a bit rock ‘n roll for sure, but I loved the drama, the swells, the foam, and the clear bits once in a while 
Staffs and Zurich have good clean swims, but no drama.
Best Bike…Lanzarote.
It’s hard, it’s got some dodgy patches of road, but it’s mostly amazing views and aero riding. 
70.3 Aix en Provence is better than all the others I’ve done but would be a fair way behind Lanza.
Best Run…Zurich.
Disappointed I couldn’t take advantage of this flat course and it is hot as hell, but you’ve got the beauty, the old town, sunbathers, the support…and did I mention it’s flat? 
Best Finish Line…Bolton
The noisiest, great setting, great build up to it.
Best after party/athletes garden…Aix En Provence
Free beer and athletes actually drinking it! 
Worst Swim…70.3 Exmoor/Wimbleball
Cold, murky, nondescript. Given the setting is so beautiful I expected more.
Worst Bike…Hever Castle Gauntlet
I feel bad for saying it, but it’s got some shocking roads that are truly painful to ride, and dangerous descents on open roads. Road bike and for those who like to suffer only. Olympic course eliminates the worst bits.
Worst Run…Bolton.
I fucking hate that run. You will never see me on that course ever again! God it’s relentless! Pass me the shotgun and one cartridge!! 
. The only thing occasionally worse is Hever Castle in the wet…because you’ll be swimming 2km.
I liked the Bastion/Gauntlet course, most of the descents are straightish. Only bit I disliked was groombridge later in the day as its too busy and due to it being a climb you are slow with cars cutting past very close.
There’s lots of good to it, but of the middle and long courses I’ve done it’s the worst.
I use it for training sometimes, where you can be more defensive. The Olympic course flows better and you can be more aggressive, even then there’s a couple of blind turns into traffic (well marshalled on race day though).