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There is something really awful about Garmin land. The reek of #midlife and gainzz.
I bought a 255s two months ago. It's fairly crap at being a watch but very good at being a node for Strava and Intervals.. validate gainzzzz.
Tl/Dr a tool for self hate
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try a Garmin watch
You can find great value Garmin watches second hand. I got a Forerunner 245 for next to nothing. As for your question about older models for the sake of aesthetics, I reckon you'd want something relatively recent so that you won't have issues syncing with your phone, headphones, HR strap and so on.
Any Garmin experts?
I'd like to try a Garmin watch, as a motivator to get fitter. The stupid whoop didn't exactly make sense.
When did they stop making fun y2k looking watches? Is there a model from the fun era that's still usable?