Here's an update for those of you still following this thread.
So, thanks to all of your OXZ/OXP suggestions, tips, advice, etc., I believe I've managed to water down Oolite to a manageable state. I have what I consider my test/non-cannon commander, just for me to learn how exactly each addon works, and see how it'll be like once I've got every piece of equipment.
It's become much easier since I started, but victories are still hard to come by, even
with the most decked out ship in my Ooniverse. I've slowly getting better though, I can tell when a ships' shields are depleted and when it's low on health. I've forced ships to warp away from a battle and even earned several kills. But often it hasn't been counted because I haven't managed to defeat a whole group on my own. I can take a couple out, but then either the rest kill me or another group of ships joins in and saves me from whoever's left, so I can't take all the credit.
Until now. I'm fresh from my first legitimate win, hard won on my own. (In game I mean. Couldn't've done it without you guys

)
I warped into a system and ran into a pack of hostiles (I'm not really sure who they were. I didn't do anything aggressive, they just flew right at me and they all turned red. No demand for cargo so they weren't pirates

) and just as our dogfight began, through open comms I saw a plea for help. I saw a ship under fire by two pirates, so I boosted over into weapons range and fired a volley at the lead pirate. The ship thanked me for the help, and sped away while its attackers peeled off to engage me. I was pitted against about 8 enemy ships, and I was certain I was going to loose.
I must've had an enormous amount of luck, because I didn't just scrape by, it was a solid victory, with missiles to spare and nearly all of my cargo still intact. One by one I picked them off, and most of them died, but a few were able to flee. I needed all of my equipment to pull it off though. Even if I was missing one part, that battle would've ended very differently. Most importantly was the ECM, about half of them launched missiles when they were low on health, and I still haven't found out how to deal with them without an ECM. When I start my real commander, it's going to be high up on my to-buy list.
Even after I bought everything I needed to fight, it was chance that got me through my first major win. I know it's going to be rough until I can grind my way up to that point. But it's going to be so much more satisfying when I finally do.
If there are any other new players who think Oolite's too hard, here's a list of addons that were recommended to me that make it easier. Maybe this'll help.
IronHide
Military Fuel Injectors
Police Scanners
SniperLock
Engine Trails
Start Choices
Telescope and Telescope Extender
Cheat Menu
Jumpgates
Combat Simulator
- Combat Balance Mod (Created during v1.8, effects were implemented in v1.82 so there may not be much difference.)
Total Patrol (only if you stay clean)