Great to see some race fans on HN!
As far as street courses go, I find for me it's kind of a hot/cold thing. The ones I like, I really like.
Monaco I think might be near the top of my must see races list every year. I watch every F1 race anyways, but Monaco just has something extra special about it. There seems to be a growing cacophony of complaints about the lack of passing but, for me it's one of those tracks that it's really the driver vs the track much more so than the driver vs the other drivers. And then of course you have the spectacle and tradition on top of that, pretty cool.
A couple in the 'States that I have always really enjoyed are Long Beach and Belle Isle (Detroit - Indy has run a Sat/Sun double header here for a number of years). Very interesting layouts and, while I don't think either is nearly at the Monaco level of a challenge, both have plenty of places where the difference between a fast lap and a wrecked car is a question of inches.
Probably more examples of street courses that just don't seem to quite work, now that I think of it. It's very easy for them to just feel a little shoehorned into the space without much visual spectacle or flow to the layout. I think Singapore, for me, is a good example. A lot of F1 fans hold that track in high regard, but I find it extremely dull and the corners to be all a bit same-y.
I have never actually attended a street race in person, but my understanding is the in person experience is generally pretty poor. Obviously, with Monaco, I think it would just be a thrill to be there soaking it all in even if you only can see a postage stamp size piece of the track. Belle Isle, as a counter example, might be better enjoyed from the couch. I don't know that for sure, but I'd certainly want to do some research on the in person experience before I book a flight to Dee-troit City.
I'm probably rambling more than a bit off topic, but I'll add as an aside that, if you ever get the chance to hit up an IndyCar race...do it. We went out to Laguna Seca a couple years back and I think I had almost as much fun as I do when I'm at a track to actually drive. We were going to either do Indy @ Laguna Seca or the USGP @ Austin and I left it entirely up to my son. I was secretly leaning USGP, but he said "Indy" immediately. For the price of a single day GA USGP pass, we got a weekend all-access pass for the Indy race and, wow, what an experience. I went assuming "all access" was mostly marketing speak but they weren't kidding. Close enough to touch the cars in a lot of cases, drivers walking right past you, etc. Hell, I met Mario Andretti! It was very cool. Race day itself was also awesome. We basically slow walked around the entire course and watched the action from every angle imaginable and then watched the last few laps from the top of the grandstands. Obviously, the experience may vary from track to track but, at Laguna Seca at least, it was 10/10.