Hmm. A couple of comments:
A destroyer to start with is troublesome. If you pilot it yourself - and don't quite know what you're doing, and sometimes even if you do - some frigates will kite you and either wear you down or run out of CR. This is going to be frustrating and/or tedious. Destroyers are also more expensive to maintain etc, raising the bar of what you need to accomplish to make a profit, let alone break even.
In contrast, a Wolf has mobility, good-enough firepower, and a high skill ceiling. If you make mistakes, you may lose quickly, but that's better than a long, boring wear-down-the-enemy-CR win. The "try something, get feedback on your mistakes, try again" learning cycle is faster.
Perhaps most importantly, if you go for the most combat-capable ships, you start with a Wolf and a Kite with an officer. A single Wolf may struggle vs 2 undamaged Lashers etc, but paired with a Kite, the fight is fairly easy once you figure out how to work with your wingman. A destroyer wouldn't be able to work nearly as well with an ally, not when facing almost mostly frigates, as you are in the early game.
The Wolf/Kite combo is effective vs frigates that have no d-mods, which is a good step above what you're mostly facing in the early game. And Luddic Path raiders, well, there's a reason you can pay the tithe to avoid the fight - but they can also be defeated with the Wolf/Kite combo. Just gave it a quick try - Wolf/Kite vs a Pather Lasher + Brawler - and it's not too tough, even without any combat skills.
That said, yeah, piloting a ship well takes some figuring out. I just know how it can be made any easier - sticking a destroyer in the fleet will hurt more than help, the Wolf is already one of the best frigates, etc. There's always the mostly-non-combat to build up a bit, too.
Ah, on a related note: these settings in settings.json can be tweaked to adjust the difficulty of "easy":
"easyPlayerDamageDealtMult":1,
"easyPlayerDamageTakenMult":0.75,