Ending Round 2, I've lost my Gladiator, which was the end of the game for me in all practicality.
In an attempt at a radical gameplay, I rammed my opponent's MC30 twice with my basic movement and again with the Engine Techs movement. Then I launch a broadsides at him post move with Demolisher. But I was scatterbrained and forgot the side facing him had zero shield, lost from the earlier attack by his CR90 at the start of the Round. His activation, he hit me with a broadsides form the MC30, had for three damage and I was done.
Had I gotten in the Engine Techs move in Round 1, and then moved forward dead center of the MC30, I could have punished him some, survived his counter-attack, and possibly escaped on Round 3, maybe even hitting the station to drop a card.
I would prefer Moff JJ as a commander. Extreme speed changes are ok but you can do that with dial and token for an occasional surprise and Jerry's extra turns at the first knuckle of the move tool mean you don't have to navigate as often so saving 12 on Nav Officers. Skilled first officers can be cheaper substitutes.
Add Ordnance experts to the GSD and look at what the Suppressor/Avenger combo can do to ships without a double brace. Finally leading shots instead of NK7s will save enough for another Tie-F or to upgrade some to interceptors.
About your last point, I think the feeling that the rebels are easier at first has to do with their available basic squadrons, which are almost all threatening against both enemy squads and ships. When putting together a basic fleet which should be at least somewhat effective, you have to decide how to deal with squadrons and want at least two credible threats to enemy ships. A couple of rebel fighter-bombers already cover the squadron-dealing and are threatening to ships by themselves, while the Empire does not have that luxury and has to put some more thought in.
But basically it sounds like your opponent went with a fleet which is more straight-forward (in the non-jousting sense ) than yours, and thus easier to use.
Try to keep it simple for your first battles: basic damage dealing ships and a reasonable squadron cover, not too many sophisticated interactions in upgrades and squadrons, and try to be as independent as possible from precise maneuvering. Maneuvering is difficult unless you have some experience, which makes the Slicer Tools Gozanti, squadron hunting Raider, and shepherding Demolisher all challenging at first. You can propably get one of those to work in your first fights, but all three at the same time is quite ambitiuous. Of course you already figured that out yourself, so I am really preaching to the choir here.
Maybe use the ISD2 with Gunnery Teams for its increased threat range, think about the GSD2 Demo for additional anti-squadron if you don't feel safe, and drop the Raider for a Gozanti and additional squadrons? Also: Leading shots and Ordnance Experts will give you the important reroll abilities and you could change Vader for Motti to make your ships tougher or Jerjerrod to help maneuvering. (When playing your first friendly games it should be no problem to proxy those cards, right?)
Basically: Try to make your ships more forgiving to the errors you are going to make at first and ramp up the necessary precision from there when you feel comfortable. Just remember that the Emperor is not as forgiving as Lord Vader - Force choking is bad enough, we would not want you to get struck by lightning if you keep losing...