hello! i'm Rob.
here in Italy and we have almost same rules as you rest of the EU (now ENAC, sooner EASA) and similar to US.
-ask esperienced pilots or experienced aerial photographers, send a mail for example worth a try.. (the old ones that did the job before drone world came out i meant)
- in order to achieve maximum manage and security about the take off and landing area, for example circumscribe the area "like for a crime".
that will almost prevent anyone cross it, civilians are safe from your LETHAL BLADES lol ( big birds or
inspire2 design is scary for most of the people that get close)-->reduces risks..
-sometimes you can get a cable to give extra safety control over the drone in order to reduce risk assestment. (just legally we know inspire are magnificent machines that will hardly fall if you're doing it right ..just a + )
-parachute
-most of airplanes take off after 6 am i guess in usa its the same not sure.... everything between 3am and 5am its almost fine (even for photography but you arleady know that city lights.... well depends..on location and subject..there are also less people (almost noone) in the street to deal with and no vehicles moving around at early dawn hours (yea i try avoid sunsets)
-use an extra operator to fly in vlos if possible, its a trick i learnt from other experienced pilots--risk assestment reduces...an observator/friend/collague will do it.
-flight terminator system ofc.. its illegal fly without. (cable is the alternative, but its too short sometimes less than 50 yards and the buffer also... )
-just to know.... its better fly with an hexacopter or octocopter....i love my inspire but still has only 4 rotors sadly..so in case of problems has less safety compared the other multicopters.. yet
inspire2 can make it no problem we know!
Im a photografer for a living and i decided to fly in the cities with quads and hexacopters and there is always something wrong that you do most of the time (legally)..depends on what you want to achieve...slowly im going...squares and big streets ....looking for the skyline its easier.....but fly above a specific building total different...most of the pictures you see in socials (90%) are illegal.
they fly with small drones like m2p or mavic air then run away, lol. its risky.
and its very sad.
infact most of them publish on social like facebook and instagram for numbers, but (most) won't publish on offical pages like national geo (just an example ) wich is what mby a photographer aims to achieve.... only the fools dare it!!!
-time ago i had my perimission to fly over a building then i went and denounced my presence to local police : "hey im here and i have a permission to fly with a drone " see the paper

.
last time police blocked traffic and let me take off..i felt i was like a special guy, but its not !!! i just did it right lots of patience...and then enjoyed watching my monitor....had to wait months...had huge satisfaction. and i will do it again.
so yet most pictures around are illegal but that doesnt stop the photography or fly with a drone...better you know what are you doing in case you are a professional.
in legal terms not just about UAV but also about the subject that you want to represent .....things move really slow..but here in italy i have to deal also with UNESCO , local laws, local police (at least 3 different, Carabinieri, Polizia, Vigili )
In the end you will get your reward dont get discouraged nothing is impossible !
.......aaaand yet i seen some pictures of the colosseum by italian ppl with drones wich i know they did it in a totally illegal way..and the same for other europeans "photographers or drone pilots that doesnt have any license." some of them had what they deserve..
still it sucks.
ridiculous is that every drone that has more than +5MP camera gets you in troubles with privacy if you dont take precautions......most of the times....being a professional actually does not allow you to take pictures freely like a normal guy..(whaat??.merely truth...go undercover sometimes...). we need ask permissions...boring boring and useless waste of time.. people with iphone X can take pictures without problems. also they say oh yes with a drone you can take pictures from above and violate privacy.
actually smartphones users violate privacy whole time..and there are even external zooms lens for smartphones, you dont even need a drone to spy or a tele lens to be stealth. all fun facts....how ridiculous the world is sometimes..
.risk or not it depends on your final aim/value project.
- just publish on social VS make serious stuff for serious purpose.
in the end...after all these words i will push on social..since..only few care about it....as you can see we have some difficulties.
this is just my little experience, im sure other people here can give you better info and share personal experience!
anyway
Looking to fly San Francisco, Boston, Chicago, Las Vegas, Salt Lake City.
i wish to see and enjoy your work i will publish mine too asap so really wish good luck with that ?