I have 3 Pebble watches paired to my iPhone (1 Round and 2 Time Steels)
Here are my pros and cons:
All my Pebbles are working.
Not many watches have as many types of customizable watch faces like Pebble
I love being able to “talk” to my watch using Snowy. I feel like 007
Add a gold watchband (be sure to match the color gold) to your gold Pebble time steel, and you’ll probably get lots of compliments.
Prices on Pebbles are great, so you can use a smart watch without spending a lot of cash.
Pebbles have great battery life.
If one day your Pebble loses what little support it has, your watch will probably be worthless.
On the other hand, some devices seem to last forever even though active official support has long gone. e.g. Zune, Kindle (sometimes, just a new battery will make it work like new)
No official support, only from forums.
(I had trouble pairing at one point, but got over that with help from forums and Pebble updates, so no showstoppers yet)
Good luck with your decision.