Great first outing! And you learned a lot too.
About keeping things dry and packing...Personally I like modularity and compression dry sacks.
Compression, because you keep volume consumption down to a minimum.
Modularity, because if it is raining you don't want to open up everything to rain all at once and also if one water proof bag gets a bad seal or cut or whatever you only get one thing wet.
So I pack in reverse order of un packing:
Bottom to top packed (Sack one goes in the very bottom of the pack):
Dry Sack 1: (Non compression)Food and cooking gear (also the heaviest so it is good to keep the center of gravity in the bottom)
Dry Sack 2: Insulation (UQ and TQ) Usually the 2nd heaviest
Dry Sack 3: Hammock and Tarp
Little Dry sack (Non compression) - Misc trail snacks and trail gear that I might need along the way
When I get to camp I always set up my hammock and tarp first then put in the UQ and TQ to let it loft. Then I get to cooking dinner. So this set up works really well for me right now.
Just my 2 cents...There is (of course) no one best way for everyone. I might try a different system as I hear other comments and trip reports.