This last city I was playing in a large region (not sandbox) the Region was named Area 51 so I grabbed my eye... Once someone in the region unlocks something it seems all cities in the region have access. Think I'm on Eastern Europe 2.
That Casino was the biggest mistake I made- I had no tourists and it was losing money big time. I started putting down monuments ("culture") and the Washington Monument was a hit, it was even profitable to operate. Then I put down some dutch windmill and it was losing money left and right.
I put up a seaport because all my factories were complaining no where to ship freight... I don't know what I did wrong because the seaport was reporting 0 usage for "days" so I finally turned it off because it's expensive to run. With no other way to ship freight that I could see I made an airport and added some cargo hangers, that seemed to work to get freight moving out of the city.
The biggest complaint around the city was "Germs" and people dying. I had a clinic and a giant state of the art Hospital with all the extras and maxed out ambulances and they were still bitching about germs... Either a bug (very possible) or it may be better to have more, cheaper, clinics than 1 big central hospital... which is BS since it is supposedly a 2km by 2km sized "city" you don't need more than 1 centrally located medical center.
For mass transit all I managed was shuttle-buses and a butload of stops. Near the end I upgraded all my avenues to carry street-cars but it had already disconnected from the server so I'm sure those are gone.
The "Maxis Manor" was a giant waste- I sent Maxis man on patrol 4 times ($2000) and he only ever managed to help 1 sim so I never even finished that challenge.
If the Casino isn't there I would start with the cheaper-to-run gambling house, probably a good thing to have before a mega-casino.
The only disaster I've seen was the godzilla thing... It knocked out some homes and a factory- it was following a line to my garbage dump- once it got there it ate the garbage in a pile and 'burrowed' down to disappear. Overall no placed buildings lost at all.
There was also "VuBot" but I released that myself on a different city doomed from the start.