I have a feeling what the answer is going to be, but here goes:
Winston-Salem
Chapel Hill/Durham
Ann Arbor
Boston
Baltimore
Dallas
Denver
Salt Lake City
Seattle
San Francisco
PICK off this list only!
1 vote for Ann Arbor: Great races in close proximity, a number of fine bike shops, great running community and excellent running shops (several), good pools and a lot of cultural benefits as well since it is cose to the University of Michigan.
Also, here in Michigan, there is a pretty hefty sale on real estate right now… 
Denver (but I would find a way to live in the city a little to the north of this city or the one to the south of the city) Salt lake would be nice as well but weather is not as nice
.
I have a feeling what the answer is going to be, but here goes:
Winston-Salem
Chapel Hill/Durham
Ann Arbor
Boston
Baltimore
Dallas
Denver
Salt Lake City
Seattle
San Francisco
PICK off this list only!
Denver first, second and third. Boulder if you can manage it, or Centennial/Castle Rock areas.
John
it has to be close to downtown for job purposes in Denver.
can’t answer with knowing your age, kids?, cultural likes/dislikes, salary, etc. Ridiculous really, but if asking I can guess the age part.
Tri only: OK, San Francisco
How do you define “best?” Training? Competition? Variety/number of races? etc. etc. etc?
I live in Denver, and I think you can’t ask for a better training ground than the front range. The variety of terrain within an hour of the city makes it possible to train on whatever terrain you want… flats, rolling hills, foothills, mountains… we have it all.
On the other hand, there is no Ironman distance race in Colorado, and only 2 HIM distances of which I’m aware. There are a handful of Olympics, dozens of sprints and lots of shorter 2 sport races (stroke and strides, duathlons, etc.). Not bad if you’re a short courser, but I prefer the long distance stuff, so I have to leave the state for anything over HIM.
Race season is relatively short (Don’t see too many races before June or after Sept), unlike say, Texas, where they race from March until November. Of course, it’s a LOT hotter a lot longer in Texas.
Competition in Denver/Boulder is stiff. There are LOTS of great triatheletes here.
People are very used to seeing cyclinst and runners on the road here, so I’d guess it’s probably a little safer here than in many other places. Yous still have to watch your ass.
I’d say I’m partial to Denver. But I’ll bet SF is a great place to be, too. If I could afford to live there, I’d seriously think about it.
it has to be close to downtown for job purposes in Denver.
Define “close”
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I would need a commute of less than 20 minutes to Denver Health, National Jewish, and CU Medical center in Aurora. Think Colorado and colfax.
SLC. You can live in Park City which is a training mecca.
I’m biased, but Denver is great. Haven’t lived on the north or east sides of town but the south and west burbs are great. Currently live in Highlands Ranch, less than 20 miles from downtown. Access to great riding and running is close by. Extensive trail network. Weather is pretty good (ran outside today in shorts and short T!) for a four season environment. Close to front range open spaces for trail running/mtn biking. Chatfield and Cherry Creek reservoirs are both close. Plenty of bike shops/running stores. Highlands Ranch in particular has a great 12 or 13 race running series including 3 sprint tris and a 1/2 mary. That said, it is primarily made up of families so if young and single, maybe look elsewhere in the metro area.
Are you limiting the list based on places that you have the option to live?
Dev
Yes, the list is a list of places I have the option of moving to.
BUT, Denver really isn’t an option for me. (I work in the healthcare field and I hated their program, I just threw it in for curiosity. I also don’t really have an option to live in salt lake)
This is where I live. 8 miles to downtown (20-30 minutes in rush hour). Easily within 20 minutes of any of those 3 hospitals. We like it… although we are the quintessential Stapleton residents, with two small kids, a dog and a decent-sized income.
San Francisco…cross the bridge and you are in God’s country for running and riding…and it is year around too. You cannot say that for any of the other cities you have listed.
Don’t you have to watch out for jet fuel poisoning at Stapleton?
San Fran. Then you don’t have to be one of those whiney bitches continually complaining about winter.
UH, not sure why you are asking me, I wrote SF not Denver.
No.
Your list is a bit Ego Centric, listing only American cities, no wonder the world hates Americans.
I vote for Auckland New Zealand (those islands just to the right of Australia) 
Year round training, huge range of bike routes around, tons of pools with great coaches, heaps of beaches for summer open water swimming, lovely climate (as long as you don’t mind a bit of cold rain in the winter) lots of bike stores and associated group rides, waaaay friendly people to train with and race against, tons of great races, including several summer series aquathons and du’s etc in the evenings after work!
We have Cameron Brown, Hamish Carter, Bevan Docherty, Sam Warriner, Terrenzo Bozone, Keiran Doe, and heaps of others waiting in the wings.
This is triathlon heaven, southern hemisphere style! What are you waiting come for a visit and see what it’s all about!