There are only a few watches out there that do music and everything else you want. Is the Fenix 5 Plus out of your budget? That is next on my list, I have a 935 and love it, but the ability to have music on the go as well looks great.
I have seriously re-considered the new Apple Watch, more because the ability to have a phone with me on long rides without physically needing to take my actual phone would be great.

Dies it need to do multisport?

Based on those 4 criteria, the answer is a refurb Series 2 or Series 3 Apple Watch from Apple. It does everything ok, but no multisport. If you move toward the mature fitness tracking functions of a Garmin, then the AW starts to fall off.

Vivoactive does not do multisport.

Vivoactive 3 is just fine for what you listed and then some. I had the first vivoactive and loved it. My friends have the 3 and its has advanced quite a bit. For lap swimming, biking, running, and whatever else you want to do it is a great watch. For OWS, it won't work, but thats alright. I actually just splurged after I had an accident with my vivoactive and got a Fenix5+. I wanted the ability to have music, but I also am wanting to step up my game with OWS more often and metrics so that is why I chose that over the vivoactive 3.

Plus I got it for 150 off during cyber week and they took an additional 20% because I upgraded my old watch :)

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https://membership.usatriathlon.org/...A2-BAD7-6137B629D9B7

Do what I did - join Tri n Sell It and Online Swap Meet on Facebook and snag yourself a like-new Garmin Forerunner 920xt for $140. You won't be disappointed.

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Nourish - Sports Nutrition Made Easy

Won't be disappointed? You're right ... except for the fact that your recommendation only meets one of very specific features list the OP mentioned.

Get a life bro

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Nourish - Sports Nutrition Made Easy

Fenix 3 has been very good for me.

Follow-up: Re: Velodrome

Let's say i'm at the Velodrome and using a rented track bike with no technology on board. Would one of these watches be able to track anything like laps, or would i be out of luck given that it's inside a building and no trip computer on the bike?

SOOL unless you fit Garmin magnet-less speed and cadence sensors. These are very portable and easily fitted and removed.

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Trust me I’m a doctor!
Well, I have a PhD :-)

My suggestion is a Lange 1 Moonphase in white gold with black dial. It won't count laps or play music, but it does keep track of the moon-phase, which if your wife is regular can also be used to keep track of when you may want to work in a few extra long rides to your training plan.

Nice watch!

As others have said, the Vivoactive 3 is the only one that hits what you want and has music, but it doesn't have any multisport capability. I highly recommend DC Rainmaker for reviews of sport watches.

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Taco cat spelled backwards is....taco cat.

That's rich, considering your reply wasn't even close to answering the question in the first place.

Still waiting on the Wahoo Elemnt Rival.... I love my Elemnt and their trainers.

Amazfit Stratos is supposed to do all that and more and is $199. Reviews suggest it's not super precise as far as OHR and I don't think there's a Spotify integration. I don't think I want a device with music but without Spotify, which isn't available on VA 3 Music (yet or ever, depending on which forum you read).

Classy, I’m partial to the Patek Nautilus 40mm Platinum...but I think the poster will be happy with anything suggested here that replaces his 305

Hey Cam —

Sorry about Lange 1 post. I’m a watch idiot and couldn’t resist. I don’t think there are many options that will meet all your criteria. With sport watches I think you can get a hall pass on size. Also worth noting the reason many of the sport watches are so large is enhanced legibility if you use them for sports. So there’s a trade off.

So if it were me I’d say:
Lower your budget to $300 for the GPS multi sport watch and something big, legible, and functional for sports.
Use the leftover $50-100 an normal time-only watch that actually fits your wrist for work and times when you want to look classy — maybe a Timex weekender for something casual or a Timex Marlin for something formal and handwound.
Listen to music on your phone.

I’d steer clear of refurbished goods unless you’re buying directly form the manufacturer with a warranty.

This doesn't fit within your budget category, but it does tick all the other boxes. I love my Garmin 645 Music. I also have smaller wrists and most watches these days that look normal on everybody else look HUGE on my wrists. The Garmin 645 has become my everyday watch. It is also great for running, swimming, etc. It does not support power meters (currently), but I use a dedicated bike computer for that anyway. Well worth a look.