As far as roadblocks, man, major cities be sewn the hell up.
I'm from Houston and it's damn near impossible to book most popular rap artist if you aren't this Jewish couple that owns a company called Scoremore, or Rap-A-lot affiliated.
Dudes like Chance, Big Sean, Kendrick Lamar, J. Cole, Wiz don't book with anybody who isn't Scoremore.
Dudes like Drake, Meek Mill, Kevin Gates, Migos don't book anything in Houston that isn't sanctioned by Rap-A-lot.
So me and partner had to start going on the road to places like Arizona, Michigan, Ohio to find these markets that really got a lot of fans but people forget they exist.
Also, a lot of venues are 

when it comes to rap shows. For the Migos show we just did, we originally had a venue that could hold 7000 people and we were pretty confident we could sell it out, but the venue found out that the Migos had a shooting at one of their concert in Vegas recently or something and was like
They cancelled our booking, we had to scramble and get a new venue, the new venue was a public city-owned venue so they were on some stiff shyt too, but luckily the little white boy we fukk with in that town had a plug to another white boy, whose mom was in charge of that venue.

She was mad cool, we assured her that we were gonna pay for enough police presence and we were going for a college kid market not a market that will bring shooters. After the show, she was damn near gonna suck me and my bro dikks because she was so impressed with how we handled the shyt.
There are so many local jokers that fukk up the rep of hiphop shows, venues are scared to book them because they associate them with violence, chaos, and unprofessionalism. nikkas be getting starstruck in the midst of these rappers not checking them and making sure the keep it professional, they be chasing hoes during the shows when they supposed to be keeping people from getting backstage, not respecting the rules of the venue.
nikka I've been around these rapper since age 19, I'm 24 now, I damn near hate rappers. I have little tolerance for the bullshyt and I'm not a square nikka. Most these rappers will respect you if they know they can't punk you, they be punking these cacs and peons. Once they realize they aren't dealing with a hoe nikka or a male bop they or their managers will usually switch their whole tone. And the cacs that run these venues will fall in love with you because you bring them that rap money they lowkey want without the bullshyt that comes with it. I'm not saying that you gotta be a street nikka, but just remember that these rappers are entertainers, not the guys that they rap about. But, it doesn't hurt to be able to bring out nikkas that are gonna handle shyt in a worst case scenario. Hell, if you aren't from that cloth, hire an big ass off duty cop to act as your personal security and they'll calm down quick.
Speaking of cops, fukk the police, BUT THE POLICE ARE YOUR BIGGEST FRIENDS IN THIS BUSINESS. If you know that you might bring out a rowdy crowd do not skimp on paying for police presence. They love events like this because they be getting like 100+ an hour to secure these shows, we spent around 11-12k to have 20 off-duty cops to work for 6 hours. But it was worth it, they being taking orders like soldiers because they want you to call them again for your next show and they can make that easy money again. The whole dynamic changes when you're cutting their check. Treat them with respect and they'll usually reciprocate it.
I swear this shyt isn't that hard, nikkas just be holding the game for themselves on some greedy shyt like everybody can't eat off this shyt. A lot of the simple stuff I'm telling nikkas on here, nikkas would hold on to for dear life. Then again it's so easy to make money in it, they want to keep it from becoming common knowledge.
The show we just did was actually supposed to make me like 135-165k initially, but the venue switch fukked that up a bit, and to make things worst the cops and management started to get

when so many people showed up for a hip-hop show, we were supposed to be allowed to bring out 5500 people and they capped us at 4000. That was a disappointment. Then the show almost got shut down because too many local ass bops (male and female) were on the stage. Once the cops told me they were gonna shut it down if the stage didn't clear, I damn near started throwing nikkas off stage like Uncle Phil. That would have been a total disaster and a complete loss on my investment.