If I had been able to sell my 1st gen, I would've considered it. I have a 42mm SS. I tried selling it with the included Milanese Loop and red sport band (OEM) at $350 and no one wanted it. I'm not 'giving' it away, so I ended up keeping it.
I remember when the Apple Watch first launched and I bought the sport model and receive it immediately. I realized I didn't like the Sport model, I sold it within weeks after the Apple Watch launched and sold it within seconds for over face value on eBay.
Now, today, the resale market is horrible. Personally, I plan on using my Stainless Apple Watch until it's no longer useful or is just manageable for timekeeping. It works for me.
I will Likely upgrade when we see a completely overhauled Apple Watch. Its rumored for a slightly revamped model for 2017 if it happens, I'm not purchasing the same design for three generations.