After JJ Season 2 and Iron Fist Season 1. Before Punisher.
Punisher needs to be part of a Wave 2 of Netflix shows. I'd argue that Daredevil, Jessica Jones, Luke Cage, Iron Fist and Defenders are enough for a first wave.
Wave 2 should debut with Punisher and Damage Control which we already know are coming and then greenlight some new series. Preferably She-Hulk, Blade, Elektra and Moon Knight on Netflix with Thunderbolts closing it out.
T-Bolts kind of needs to be last because I'd like to see Phase 3 and part of Phase 4 building up the T-Bolts roster and have The Raft built as a place where they can all meet before being broken out.
We already have Baron Zemo, Crossbones, Blizzard and Mister Hyde in the MCU, it only makes sense to finish the roster.
I'd make the Spider-Man reboot start with Joystick as a random robber in the first scene who won't appear again until after the credits. Then I'd adapt Amazing Spider-Man 19 and 20 with Scorpion as the big bad who's supposed to be the responsible government registered alternative to Spider-Man and then rebels when he learns that his powers are slowly killing him. Scorpion and Spider-Man start off both trying to apprehend the Shocker but Spider-Man and Shocker join forces to stop Scorpion in the climax except Spider-Man still apprehends Shocker since he IS a thief. They all meet in the Raft after the credits with Zemo and Crossbones.
Beetle should show up as the villain in Ant-Man And The Wasp and have Taskmaster as his henchman. Beetle should be apprehended while Taskmaster should go on to appear in Agents of SHIELD and Iron Fist before appearing in T-Bolts. Once again, Beetle should be on The Raft after the credits.
Atlas should first appear in Luke Cage Season 2 and once again, he should be apprehended and sentenced to appear in The Raft.
Taskmaster should reappear in Agents of SHIELD and Iron Fist as a minor villain before he's also thrown in prison.
Bullseye is the most obvious choice for a villain for Daredevil Season 3. Matt should drop him off a building, then visit him in the hospital to play Russian roulette but stop short of killing him and instead just carve a symbol into his forehead. He's naturally get sentenced to The Raft.
Ghost should pop up in Iron Man 4 as the new Iron Monger's henchman along with Spymaster. Spymaster would die and Zeke Stane would be taken into government custody as a glorified slave. Ghost on the other hand would be put in the Raft and get a third post-credits scene where he's introduced to Zemo, Beetle, Bullseye, Shocker, Crossbones, Joystick, Atlas, Ghost, Taskmaster and Scorpion.
I'd have Thunderbolts start with Mister Hyde, Blizzard and newcomers Songbird, Jolt and Moonstone being hired to attack The Raft and stage a jailbreak. Grant Ward wanted Zemo to once again lead HYDRA because they're fractured and weakened and they have bigger threats than just SHIELD to worry about with AIM, The Hand, The Maggia, rogue HYDRA cells, etc.
I'd want Moonstone to show up in T-Bolts as opposed to Captain Marvel because I want Captain Marvel 2 to adapt Live Kree or Die and bring Ronan back from the dead. Something where Carol is forced to allow herself to be put on trial to avoid an alien invasion and fights off Ronan and the Lunatic Legion after the events of her first film. War of the Marvels should be saved for Phase 5 since Phase 4 should be the breather and Phase 5 should adapt Dark Reign as a phase-long story. That and I just like Ronan and want him to get more character development since GOTG kind of made him into too much of a generic bad guy. Jolt doesn't work unless she's naive enough to believe that the T-Bolts are actually the good guys and I can think of much better stories for Captain America 4 than anything involving Songbird. She's much more interesting as an anti-hero than a villain.
As for casting the T-Bolts, I won't list the members already cast and Jason Biggs is already rumored for Scorpion.
Songbird - Michelle Trachtenberg
Beetle - Donald Glover
Taskmaster - Cam Gigandet
Joystick - Felice Herrig
Bullseye - Ray Park
Ghost - Don't care since he never takes off the helmet in the comics, I'd even take a woman.
Shocker - Daniel Tosh
Moonstone - Viva Bianca
Atlas - John Cena
I can't think of a good Jolt who isn't too famous for TV. We need somebody young to both have a connection with Blizzard and to contrast with the 30 and 40-something crooks and the much older Mister Hyde. Can anyone here think of an Asian female actor who's incredibly talented, in her 20s and can appear innocent enough to genuinely want to do good while surrounded by bad people? I feel like a former Disney Channel, Nickelodeon or ABC Family star would be a good choice but I'm not familiar with their output.