I would say I got comfortable with signaling at about 700-1,000 miles. I wasn't able to stand for a couple of years. And I still don't stand on big climbs... it takes too much energy and hurts. I can spin up just about anything, but I do stand on short rollers.
After 10 years, I am still not so good with the bottle. Yea, I know what to do, but my coordination kind of sucks. I still prefer to stop. If it's a flat road and I can slow a bit, I'm OK.
Riding in groups and commuting to work got me over the fear of traffic. While I don't ride in downtown Boston, I do ride in suburban traffic and in some situations I would have never dreamed of just 3-4 years ago. I feel pretty confident, too. I am very cautious and safety oriented, and I don't really care what others think.
2015 Trek Silque SSL
Specialized Oura
2011 Guru Praemio
Specialized Oura
2017 Specialized Ariel Sport