Following up on the "to match" part:
Android Wear watches (like the Hwatch) are compatible with pretty much all Android watches running Android 4.3 and beyond. So, there's no concern about matching the Hwatch unless you're talking about some preference to have phone and watch from same manufacturer for style reasons.
Here are some comparisons:
I'm in the same category as The_Chief... never used a Gear S2 only used my Android Wear moto 360 version 1. So feel free tos discount my comments accordingly.
My preference for Google vs Samsung ecosystem:
My Samsung phone came with a lot of Samsung apps (S-voice and S-note) and a lot of google apps that do the same function. I tended to use the Google apps (example voice commands: note to self, set a reminder... set an alarm...) over the Samsung apps, and I make heavy use of them. The same voice commands that I'm used to on my phone are also available on my Android Wear watch (with a few exceptions). So I tend to have a belief that things are simpler in the long run if you focus on one "ecosystem" and google has always my preferred ecosystem since I got my first Android phone. That would tend to steer me towards A.W. vs Samsung Tizen watch, all other things being equal. You might say: but my Samsung phone works fine with all my google apps even though I didn't get a Google nexus. But it's not the same: Samsung phone is Android os which is fully compatible with google apps, while Samsung Gear S2 watch has a different os (Tizen), not compatible with watch apps on Google play.
If you are inclined to follow oleb84's recommendation to dip your feet in the water more slowly with a less expensive option, there are at least two fine options on the inexpensive side for Android Wear (see A and B below).
A - Moto 360 generation 1 - $99. It's round and the price is right. That's what I have.
The three downsides you may hear are about the Moto 360 G1 compared to other A.W. watches:
1 -Slower or less responsive than other A.W. phones due to processor.
2 - Flat tire shape
3 - Less battery life, due primarily to inefficient screen technology ips lcd, gives no energy savings for pixels not lit up or not white (unlike amoled which uses power only for the pixels that are lit up, and saves more power for colors which are not white)
My opinion on these three downsides:
#1 - I don't notice 1 at all. It is plenty fast /responsive for my purposes of heavy use.
#2 - I don't notice 2 at all except when people on the forum or people who have been smartwatch shopping comment about it. If it really bothers you there are plenty of watchfaces that completely mask the flat tire shape of the display.
#3 - I do notice #3, because of the way it forces me to use my watch. On this watch it is almost a necessity to let your screen timeout to dark (not dim) quickly after use (10-30 sec) or else you will burn your battery way too fast. That means most of the time your gorgeous watch is a hunk of unlit lcd screen on your wrist (this is my biggest complaint). Also it takes a second or so for the screen to light up when I tilt my wrist (a minor complaint). So I get fine all-day battery life with the screen timing out after 10 seconds, but it doesn't look great to have a deenergized lcd screen on my wrist all day. That complaint falls in the category of appearance/style. In terms of functionality and usefulness, I'm loving the many small ways that it makes my life easier.
B - If you were inclined toward rectangular watches, the Asus Zenwatch is another one that is on the inexpensive side ($130-$150). Some people find it very stylish. I almost bought a Zenwatch, but my thought was that I didn't want to draw a lot of atttention to my watch (the Moto 360 does a better job of not drawing attention than the Zenwatch imo). The Zenwatch has the amoled display so doesn't have disadvantage #3 above.
