I have had the 38mm Sport for 4 months. I do like the blue Sport band that came with it, but usually I wear it with a nicer brown leather buckle strap from Clockwork Synergy, or a leather loop knockoff. I tried on the SS with a leather loop in the store, and yes...I agree that it is a big step up in terms of look and feel. Yes there is a weight difference, but one would get used to that quickly. The SS version is easy to covet... especially since one of the things I like about the Apple Watch is that it looks less sporty or tactical than many smart watches and fitness bands on the market.
Personally I wish that I had spent the extra money on the SS, but I am probably going to wait until the next version of the Apple Watch. I went with my head more than my heart. I could sell my sport and upgrade, but now isn't the time for me to spend hundreds of dollars I don't have to spend. Besides, I usually don't think about it. I think the Sport looks fantastic. It does not look cheap to me, unless you are looking at it sitting right next to a stainless steel model. The Sport with a leather band also fits my casual (but not too casual) mode of dress. However the SS model would fit my style even better, and it is nice to splurge a little every now and then... especially when it's something you wear every day for 15 to 18 hours straight. When you look at it from a daily expense perspective (spread out over two years), it's just a difference between roughly 50 cents a day and a dollar a day (even less if you sell the watch after 2 years). Based on all the little conveniences I get out of my watch every day, what's an extra 50 cents?
Of course you have to pay up front, so when you look at it that way you really are paying twice the price for a device that does exactly the same thing. The SS will be more durable, but Apple Care + is cheaper. My advice to people who want an Apple Watch: If you are on a budget, the Sport is still a great smartwatch for half the price; and it dresses up nicely with inexpensive third party bands. If budget is not a huge concern, try them both on in the store. If your heart says "meh" about the SS, get the Sport. If your heart wants the SS, ask yourself if you can spend the extra 50 cents a day.
Sean