Oooo that’s a dangerous conflict of interests 😛
The problem isn’t just the conflict of interest, but internal conflicts. Stormtroopers are described as accurate, the Empire is supposed to actually be powerful and dangerous, the Imperial Navy is supposed to be fearsome. Yet apparently neither their foot soldiers or starships can hit jack crap at nearly point blank range against targets moving in a straight line!
A lot of this comes down to plain movie tropes and ‘the future blows’, i.e. in Perfect Dark where every single personal weapon has less power, ammunition capacity, accuracy and range than real world weapons from WW2. Star Trek has this problem from time to time, especially the Next Generation: a hand phaser is supposed to be able to vaporize an office building in one shot, and yet Star Fleet officers who are supposedly the best of the best can’t hit some dude 25’ away with a recoiless beam weapon that continuously fires when the button is held down. Not even Data, the android superman! If these scenes were done in a realistic way it would be like something out of Terminator, with Data stunning 12 guys in 12 seconds and nobody even finding it remarkable. Indeed, Terminator 1/2 are some of the only science fiction movies where weapons, vehicles and killer robots are not routinely inferior to real world people - and the reason is obvious, because if future tech is portrayed realistically then computers would run everything, every ship would be hit by every shot and blow up in one hit. This is pretty accurate to modern technology - the only reason Air Force fighter-bombers don’t get blown out of the sky more often is because they’re fighting people with no air force and no large scale anti-air defense. Missiles generally don’t miss their targets (at least the good ones), they can turn faster than any human-piloted vehicle could ever hope to, and one shot is MORE than enough to instantly incinerate any realistic air vehicle (and generally tanks, too!) Realistic military and automation technology tends to render people irrelevant (or at least resigned to strategic and not operational roles), and such technology would not only be implied but actually necessary to operate a vehicle moving and fighting as fast as science fiction craft are supposed to be. I’m a big fan of hard science fiction, but it’s certainly a whole different reality than space operas and ‘lasers and feelings’ fiction.
If weapons and militaries were shown to be realistically competent (or even realistically incompetent!) James Bond would have died in the 60s under a hail of 7.65x39 bullets.
So you basically have to either conclude that Obi Wan is an idiot with no judgment and the Rebellion sucks utterly because the Empire are a bunch of clowns, or the characters are extremely lucky and/or contrived circumstances assist them.