It is good to see some fresh thoughts and plans flowing.
On worker actions after completing the sheep pasture, I agree with mining the grass hill. It will give us a third strong tile for the capital, and we will want to grow larger after the settler to take advantage of it. Probably by building another warrior. I think it should work out just about perfectly: Finish settler, then build warrior while working the two pastures for +6F/turn. We will have 2 food in the box after growing to size 2 next turn, so 4 turns should see Silver Lining grow to size 3. At 4 hammers/turn we should finish the warrior at the same time we grow to size 3. We can then build another settler (to claim whichever of wheat/northern site we did not take first, if it is still possible) or a worker or whatever.
So we could work the sheep tile (2F1H1C) rather than the forested sheep (2F2H) and get a little more commerce. I am not sure this is worth it since we are talking 5 turns, so only 5 beakers difference. That is about half of one turn's research right now. I think I would rather have the hammers as 1/3 of another warrior, or the start of a barracks. But we could take the commerce instead if we wanted. Once we plant our second city our research will have to drop from 100%, so maybe getting to BW one turn earlier would be useful?
I think the chariot rush explanation for TSR makes sense. I don't see how they could possibly get to BW early enough for an axe rush by T51. Maybe if they settled where they could work a coastal tile for more commerce? Otherwise I can't see BW finishing before ~T40 at the very earliest, leaving no time for building the axes. But I don't see how they build that many chariots in time, either. Well, I guess a mass chop fest after finishing BW around T40-42 might do it. But where to get enough workers, since they have grown a bunch of pop in the mean time? Can't chop additional workers without BW, can't grow while building workers...hmmm.
On the site for city #2, I still like by the wheat. Grass wheat, grass horse in first ring makes for excellent food for rapid growth, would already be connected by the existing road for some extra commerce (which we really need), and of course provides horses right away and elephants later once we can pop borders. The northern site has plains cows and plains horse, which will provide very good hammers but is rather short on food and will therefore grow rather slowly.
The northern site would help prevent us from being boxed in, keeping a path to further eastward expansion open. But if we are planning to rush a neighbor (or two, or three) then we do not really care about being boxed in by AI cities. We will take those cities for ourselves or raze them.
For the bear...not sure. I don't really like the odds defending on the forested hill, even with a couple turns of fortification. And I dislike risking our CG1 warrior doing it. We could send the new warrior in that direction, to give us two warriors available -- should pretty much guarantee defeating the bear although we could lose one of them. But I think it is better to just avoid the bear, and hope it is killed by an AI unit or eventually disappears as animals do after enough turns.