Pebble Time Round reviewed: You can judge this book by its cover

Pebble's newest smartwatch is mostly different in design—and that's the point.

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Pebble watches have a devoted following. (I used to own one, OG, before it died.)
Some things that point to the profile of a happy Pebble watch customer imo.

1. The screen is most visible in bright light outside. It's reflective.
But it is accepted that in medium to dark conditions the backlight washes out colors on the Time (TS) and Round.
2. Long battery life except for the Round (which is average).
3. Good water protection except of the Round.
4. It's OK that Pebble Time (TS) and Round have the biggest smartwatch bezel ratios.
5. Accepting that customer service is e-mail only. And CS response times can easily take a week +.
6. Pebble watches are cheaper.
7. It's OK that Pebble watches have more limited functionality compared with the Gear S2, Android Wear or the Apple Watch (no answering phone calls just using the watch paired with the phone, no NFS pay system, no assistant like Google Now).

The only thing on this list that I couldn't deal with was the week+ lag in the e-mail only customer service.
Otherwise I'd probably still be a Pebble watch owner.

edit; clarity

 

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_fluffy[/url]":30mdb0bg]I was one of the Time Steel backers, and ended up going in on the "preorder TIme Round, get $50 off, risk-free" deal.

I love the fashion of the watch, and the battery life doesn't bother me, but there's one reason I'm probably going to return it: the damn thing just will not stay connected to my iPhone. I've contacted support and completely redone the pairing many many times and yet it'll just connect for a few hours and then disconnect.

This is supremely annoying and completely negates any benefit of having a smartwatch, so back in the mail it goes.

That's the kind of thing which turned me off to Pebble. Your watch seems to be defective.
Your problem could be fixed with a quick exchange if there was store or phone customer service.
But dealing with Pebble has to go through their e-mail only customer service. The owner has to provide pictures of the problem and often wait over a week.
If there is no response, then some customers go on the Pebble forums asking for faster support.
I find that annoying.
Still some people don't mind waiting weeks getting their malfunctioning watch replaced.