This is a bit of a gripe I've had for a while, and it was...slightly addressed with the update to 0.91, but the way bounties scale is way out of wack.
Essentially, what we have right now, is a bounty system that scales vaguely linearly with what I assume to be the player's level, which is fine as long as any given campaign goes smoothly and the player never makes mistakes, or savescums heavily when they do.
The problem happens when you do make a mistake, in my current playthrough I have fleetwiped twice now, and I kind of like the game when it is forcing you to adapt to unforseen circumstances, so I tend not to revert my save when such things happen, and with the tease of story points and the lingering ironman mode, I get the impression that at some point, this is how you are supposed to play the game, bask in the successes, and roll with the punches.
This is where the issues with a level-scaling bounty system come into play, as right now, after my second fleet wipe, followed by a cycle-long grind to get my ducks back in a row, the bounty board currently looks like this.
and it has prettymuch always looked like some form of that since my first fleetwipe. The moment you are set back in a campaign, bounties (outside of the system bounties of course) become totally blocked off as a means of earning income, because the system seems quite clearly geared to always provide bounties based on your level, with a single, bottom tier bounty that doesn't really pay you enough to get back on your feet in a reasonable length of time, moreover, all the destroyer/cruiser fights have all but disappeared from the board, fleets either consist of a few frigates, or contain multiple capital ships with VERY few exceptions, which poses a problem from to fronts for my 2 cruiser/ smattering of destroyers fleet.
My issue is only half that this makes it difficult to do bounties, the other half is that this seems so consistent as to be kind of gamey, where it doesn't have to be. I doubt crime lords are watching my career with bated breath, and fielding their fleets accordingly, it would be far more interesting if some cycles things were just like this, while other cycles there's nothing but rockstar rookies skulking about drawing the ire of the law, and of course, there should also be times when approachable bounties are plentiful, in perfect balance with the strength of your fleet...or well...vaguely balanced, like I said, variety here is key.
Also to clarify, this is mostly to do with targeted bounties, system bounties I really don't have anything to complain about except that they can be kind of short. Usually by the time I'm on the scene, either the AI has mostly cleared them up, or the pirates are still about but there's only a week or so left to cash in on it before its gone.