I really appreciate the replies!

As an update, this week went quite well, I think the Summer Music Camp at Church was an important milestone as it was the first time we've ever dropped him off somewhere (well besides with the nanny or family) and totally left the area (we've done child care at the gym and church but we've always been on site nearby, this time we were a full 30 minute drive away at home). The teacher did mention that he was "very independent" on Monday, but she said that was fairly normal for the first day since he wasn't used to the structure yet.
My son later told me he got put on time out at one point that day because he was trying to take out toys when he wasn't supposed to. On Wednesday (his 2nd day of camp) my wife said the teacher indicated he was still a bit challenging but showed significant improvement over his behavior on Monday. Today when I picked him up on his third day the teacher said "he did really well" so I think he got settled into the routine. It was pretty cool, each day they got to make a different instrument and they learned songs, played games, etc. He really likes it, he calls it his "song school". He seems to relish the idea of being away from his brother during the day, he told him this morning before we left in a teasing sort of tone "you will not see me today [brother's name], I will just be gone at school".

At home I have been focusing a little more on teaching him phonics and sight words which he seems more ready to learn now than he was in the past when I had first introduced those subjects to him. He likes the Curious George sight words program we have which includes a bunch of easy readers and a sticker chart poster (he loves earning the stickers!). He impressed me when I was pointing out the word "bat" as in baseball and he says "that's just like the nocturnal animal!".

I also took him for a nice hike up to some cave rocks on Thursday which was fun as we got to spend some time in nature together talking one on one which we haven't really done before.

Today after his music class I took him out to eat at a local German cafe for the first time and we played a couple of games of chess there since they have pieces and boards at some of the tables, the other patrons were rather impressed and asked how long he had been playing to which I responded to their surprise, "since he was 2"; they were very encouraging and told him to keep it up! He was a little shy but he did quietly say a couple things in German like "danke" and "auf wiedersehen". As we left he also noticed a small map of just the country of Germany on the wall by the door and said "look Dad it's Germany!".