Apple watch on my mind. Never had one. Considering a Refurbished Series 5 GPS 44mm for $369. I realize there will probably be a new watch coming in the fall. I probably wont do a lot of fancy stuff with the watch. And I usually have my phone with me, and on familiar wifi networks. Calendar and Reminders and some health and fitness tracking will be my main reason for having it. Should I wait? Will there be a price drop on Series 5s when the new one comes out. What else should I consider before buying? Many thanks for your input.
I’d suggest that only Apple knows the answers to most of your questions, and they aren’t talking much about it yet. They haven’t been on a downward trend for pricing new watch releases – so, history might be a guide.
But if your needs are minimal, get the refurb 5 of even a 4. They are perfectly serviceable and good watches. Just be sure you get some sort of warranty or ability to return the device from whomever is selling it.
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Looks like you’re leaning towards the refurb one, so go for it and see if you like the experience.
September 2021 is not so far away if you discover that you are going to do a lot of “fancy stuff” on it and want the latest and greatest. 
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Then I agree with @anon41602260 and @memex, a refurb should be a good choice for you. I use my Series 2 for notifications, controlling podcast/audible playback, workouts, timers, sleep tracking, weather, Siri, etc. I normally charge it in the morning while I shower, etc but it will generally last until late afternoon if I forget.
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There’s bound to be a new Watch coming out within 3 months. If you’re happy with the current model and want/need to buy now, buy now.
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