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The main advantage of getting a S8 now is that you can buy a certified Apple refurb.
When I got my S8 a few months ago, a refurb was very close to same price as brand new from a large UK retailer. Not always the case, I know. But I decided on brand new.
 
My perspective having just bought a 2nd hand S6: Shop had a SE2 & S6 both for £160, I was strongly considering the SE2 for the newer chip and lasting some more releases but having been used to the always on display of the Bip I was using I opted in the end for the S6. (As it turns out I lucked in and got a 2nd hand watch with a 98% battery health and only 94 cycles and no scratches)

I chose to get a watch now to see if I would like what it did compared to my Bip (going from 30-45 day battery life to 3/4 day), and if I would get on with it. I didn't see anything really in the updates that made paying more for a S7 or S8 worth it atm.

The intention then being to later sell the S6 and get a new S9/10 or Ultra 2 or 3 down the line. (Or maybe refurb Ultra if they ever appear on the Apple Refurb site).
 
I'm on the same boat and decided to wait for S9.
They will announce the new one in less than 3 months.
 
I was gifted a Series 8 for Father's Day and I'm happy with it. If you need one, I'd say go for it. But if you can wait, then hold off and see what Apple announces with the Series 9.
 
My wife has S8 and likes it very much, much better than SE1 she had before.
S8 should have the best HR monitor of any watch, according to a test I saw.

To the person that picked a S6 over SE2, if prices were similar, he/she did a great job: AOD is very useful and you have ECG and SO2 but no car crash detection (it can come from a recent iPhone though) and maybe a shorter OS support.
Returning to the original question, I think it depends on how much do you need a watch this summer. If you already have AW wait for the upgrade or possible discount on S8. Otherwise, if you plan to use AW this summer you can go with a great product.
 
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There's never a bad time to buy into latest-and-greatest Apple Watch. I wouldn't hesitate. If you see something about the Series 9 you absolutely must have, upgrading is easy and affordable with trade-ins.
 
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Ask Siri to flip a coin! 🙃

Moose makes a good point. There might still be inventory of new Series 8 at that time, even cheaper than they are now - though with less selection.
Selection will probably increase won’t it, with people pushing their S8 to the second hand markets to afford their new one
 
There's never a bad time to buy into latest-and-greatest Apple Watch. I wouldn't hesitate. If you see something about the Series 9 you absolutely must have, upgrading is easy and affordable with trade-ins.
Unfortunately you can't trade in an Ultra for a Series 8 as far as I can see
 
Outside of used watches, I doubt we'll see the Series 8 go too much lower in price than it is now. Looking at MacRumors articles on S7 pricing after the S8 released and comparing that to the current S8 pricing.

October 2022:
Comparatively, not many GPS models of the Series 7 are seeing notable discounts on Amazon this week. The best deal can be found on the 45mm GPS Apple Watch Series 7 for $309.99, down from $429.00. This is an all-time low price and it's only available in (PRODUCT)RED, but it has a delayed shipping estimate as of writing

June 2023:
Lastly, solid deals reappeared on the GPS models of the Apple Watch Series 8 this week, starting at $329.00 for the 41mm and rising to $359.00 for the 45mm. These are both all-time low prices on the Apple Watch Series 8, and they're available in multiple colors and sizes.

A $20 savings on a previous generation watch with limited selection and delayed shipping doesn't sound compelling. If I planned to buy the Series 8, I'd just do it now.
 
I had a Series 4 Nike+ and decided to buy an 8 when I saw Amazon selling them for the same price Apple sells the refurbished on their website. No regrets
 
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If you’re in cars a lot and don’t have a 14 get the 8 now for crash detection. Unless you travel with someone who has a crash detection device, then wait for the 9 to decide.
 
My wife has S8 and likes it very much, much better than SE1 she had before.
S8 should have the best HR monitor of any watch, according to a test I saw.

To the person that picked a S6 over SE2, if prices were similar, he/she did a great job: AOD is very useful and you have ECG and SO2 but no car crash detection (it can come from a recent iPhone though) and maybe a shorter OS support.
Returning to the original question, I think it depends on how much do you need a watch this summer. If you already have AW wait for the upgrade or possible discount on S8. Otherwise, if you plan to use AW this summer you can go with a great product.
That was me :) Car crash detection not so relevant as I don't own a car, or know how to drive. As to recent phone, got the SE2022 last month.
 
Got my Series 8 45MM GPS in red for $309 Amazon Prime Day today with 5% off Amazon Visa shipped free arrives tomorrow. With sales tax, $312 total. Close enough.

The battery in my S4 is awful. It’s time.
I’ll look into replacing the battery for a sleep tracker.
 
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I currently have an S5 and I'm waiting - at least to see what the S9 brings, and if I'm underwhelmed the plan is to pick up an S8 at a good price.
 
What did you decide to do, OP?
I go back and forth but I guess I am waiting. Was really hard not to get the 45mm Series 8 GPS on prime day as it went down to £379. I plan to get the 15 Pro Max so waiting for series 9 makes more sense especially if it does get a new chip, also series 8 is still £399 that was the price on launch day for the Series 7 so it doesn’t make sense buying a watch now that’s 10months old at nearly full price.
 
I go back and forth but I guess I am waiting. Was really hard not to get the 45mm Series 8 GPS on prime day as it went down to £379. I plan to get the 15 Pro Max so waiting for series 9 makes more sense especially if it does get a new chip, also series 8 is still £399 that was the price on launch day for the Series 7 so it doesn’t make sense buying a watch now that’s 10months old at nearly full price.
I’d wait if I were you, mate.
 
I was one the fence about the Ultra when it came out and bought a Fenix 6 Sapphire instead...which actually didn't do anything for me that my old Fenix 3HR didn't do....so I sold the Fenix 6 today and I'm going to wait for the release of the Ultra 2...I'm using my AW6 in the meantime...great watch especially for value$$
 
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