If you are not carefully covering your tracks, then there are a number of ways for law enforcement to track your online activity and eventually tie you to your wallet address. That being said, it is possible to remain anonymous, and it is certainly a lot easier to do so compared to fiat.
But let’s be honest, most people are not looking to do that. Most people are not looking to break any laws and are only interested in a simple, fast, cheap and secure method for transfer/payment/storage that offers some privacy and will allow them to take control of their own money in lieu of having banks and other groups decide what they can/cannot do with it, while getting hit with fees and other charges that are created and imposed for any reason, at any time etc…
Regarding Ulbricht, it is my understanding that law enforcement conducted illegal search and seizure, so that may not be the best example in this case.
Regarding ICO’s, I was able to invest in some, early-on, but more and more ICO’s eventually started rejecting US participants, outright. I even invested in some ICO’s that later told me, after-the-fact, that I was not eligible, and sometimes had to jump through hoops in order to get my initial investment back.
I am part of an investment pool and those of us that are Americans have magically transformed into Canadians overnight. No harm, no foul. Certainly easier to do before everyone started implementing sophisticated KYC methods that utilized mobile camera devices for identification verification purposes. It is ridiculous that we would even have to stoop to such levels just so that we can invest our own, hard-earned money how we see fit.