Both characters were played with iron mode enabled, normal start, full damage, and max fleet size.
Bounty Hunter Playthrough:
Early game -
Enjoyably Challenging. The initial 3000c per frigate bounty in Corvus got me a good start. Bounty hunting nets good income, but expenses for repairs, travel, upkeep, and new ships frequently made my financial situation volatile. I destroyed something like 20 named bounty fleets before ever seeing one with a bounty of more than 30k, that's when things got easy.
Mid game -
Cakewalk. The payout for killing named bounty fleets suddenly jumped from 30k to ~70k, but the fleets themselves were only marginally more powerful. Larger bounty fleets had often taken serious losses before I arived, meaning I frequently earned oodles of money for trivial fights. Military markets started opening up, offering combat cruisers that easily steamroll the weak (D) ships.
Smuggler and Aspiring Drug Lord Playthrough:
Early game -
Easy. Lacking the scruples to avoid the black market makes it really easy to turn a decent profit, even with very little cargo space. There's no risk of combat casualties and only minor risk of unprofitable investments due to the ability to side-step tariffs. I amassed a small fortune of over 300k before everyone started hating me.
Mid game -
Brutal. The pirates begrudgingly tolerate me now, but half the legitimate factions won't trade with me anymore and the other half try to kill me on sight. Smuggling is much more difficult now that I can't even dock unless no patrols are nearby. I'm struggling to work my way into the good graces of the pirates, but they keep falsely accusing me of smuggling at pirate stations, which periodically worsens my reputation with them. All the worthwhile trade fleets always seem to be too well guarded for my small fleet of frigates to take on, so I haven't even tried proper piracy yet. The only destroyers anyone seems to be willing to sell me are the crippled (D) versions, but I recently had the good fortune to find a rare Madusa on the black market. I'm looking forward to finding out how the game changes now that I have the power to kill those pesky patrols and succulent traders