I love my Apple Watch, but when I did wear a mechanical watch (I have to think back to the 1990's) I wore a simple analog watch with a white face, stainless steel case, black numbers, a date complication and a canvas band very much like your Timex and probably in the same price range. In fact it might have been a Timex. The look of your $40 Timex is iconic - a no frills basic watch that is nonetheless elegant in its simple but functional design.
I stopped wearing such a watch in the late 1990's when I began to carry a cell phone and a PalmPilot PDA. I still wore a watch for some time while carrying those devices, but eventually the watch either got lost or stopped working and I guess I just didn't see the need. Not only did I have two devices with me at all times that had clocks, but everywhere I went I was surrounded by wall clocks, computer displays and appliances with clocks. After more than 15 years of not wearing a watch, I can definitely say that I did not buy an Apple Watch so I can check the time! I bought it mostly so I could avoid digging my iPhone out of my bag or pocket a couple dozen times a day just to glance at information like my calendars, reminders, task list, text messages, and (on occasion) even the time. The Apple Watch isn't really a watch at all. It's a wearable computer that can tell the time. I know that you know this and your point is whether or not that wearable computer offers enough utility and convenience to replace a plain old watch on your wrist.
Personally I find your gripes about the AW to be non-issues in my life. I have never had trouble flicking my wrist (or even just rolling it works) to check the time on my AW. It always comes on using the same natural movements I used when I had a conventional watch. No it won't come on if your wrist is perfectly still, unless you tap it. Either way I find checking the time to be convenient. As for sending a negative social queue when checking the time in a meeting or a conversation, conventional watch wearers have this problem too. I see people with conventional watches glancing at the time on their wrists quite often in meetings. Yes a smartwatch will give you more reasons to glance, but how hard is it to wait until a more appropriate time to sneak a peek? One reason I like the watch is that the gentle tap of the haptics doesn't seem as urgent as when I had audible notifications on my iPhones. With the Apple Watch I frequently ignore the tap-tap and wait until a more appropriate time to view my missed notifications. When I want to check the time I will usually look at the laptop or iPad I am using (since I frequently take notes on one in a meeting) or I will glance at the clock on the wall. Charging is also no issue because I would put the watch in its place when I go to bed anyway, and in this case its place happens to be a charging stand. My watch never runs out of juice before the end of the day. While damaging the watch is certainly a concern, I have found that it is no worse for the wear after 5 months. Just get Apple Care + and don't worry about it.
You are absolutely correct that the AW (and all smart watches) will be much better in 5 years, but in my opinion it is already one of my favorite technology devices ever. I would absolutely buy it again in its current version.
As an aside I am also a cyclist, so I checked out your AW cycling article. I have tried several apps (including Strava) in addition to just using the cycling workout on the AW. I have been a cyclist since the early 1980's and did some amateur racing for a few years in the late 80's and early 90's. Then I shifted more towards mountain biking, road touring and recreational road riding. Over the years I have gone back and forth about using cyclometers. I have used them at times and found it inspirational as far as encouraging me to log more miles or improve my average speed and cadence (especially when I was racing or just trying to lose a few pounds). Usually I have adopted a more zen-like approach of just riding without worrying about the speed or the miles. I think the last time I used one was probably in the early 2000's. I need to lose a few pounds, so I have been using the AW to track my walking, hiking and cycling. The basic workout app does a very good job tracking bicycle rides but of course it lacks some of the metrics provided by apps like Strava (most notably the elevation gained during a ride and a map of the ride). I have been meaning to try Strava, Cyclemeter and Runtastic again to see how they have improved. Last time I tried them was in August and they all had their bugs or stability issues.
Sean